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WO2020244969A1 - Dérivés de pyridine et leur utilisation comme fongicides - Google Patents

Dérivés de pyridine et leur utilisation comme fongicides Download PDF

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Publication number
WO2020244969A1
WO2020244969A1 PCT/EP2020/064576 EP2020064576W WO2020244969A1 WO 2020244969 A1 WO2020244969 A1 WO 2020244969A1 EP 2020064576 W EP2020064576 W EP 2020064576W WO 2020244969 A1 WO2020244969 A1 WO 2020244969A1
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alkyl
alkenyl
alkynyl
halogenalkyl
cycloalkyl
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Inventor
Georg Christoph RUDOLF
Michael Seet
Bernd Mueller
Wassilios Grammenos
Benjamin Juergen MERGET
Andreas Koch
Nadine RIEDIGER
Christine WIEBE
Thomas Grote
Jan Klaas Lohmann
Christian Winter
Anja Weber
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BASF SE
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BASF SE
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    • A—HUMAN NECESSITIES
    • A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
    • A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
    • A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
    • A01N43/34—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one nitrogen atom as the only ring hetero atom
    • A01N43/40—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one nitrogen atom as the only ring hetero atom six-membered rings
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
    • C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
    • C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
    • C07D213/60—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
    • C07D213/72—Nitrogen atoms
    • C07D213/75—Amino or imino radicals, acylated by carboxylic or carbonic acids, or by sulfur or nitrogen analogues thereof, e.g. carbamates

Definitions

  • the present invention relates to the use of pyridine compounds and the N-oxides and the salts thereof as fungicides as well to new pyridine compounds.
  • the invention also relates to the composition comprising at least one compound I, to the method for combating phytopathogenic fungi and to the ssed coated with at least one compound of the formula I.
  • Another object of the present invention is to provide fungicides with improved toxicological properties or with improved environmental fate properties.
  • the present invention relates to use of the compounds of formula I
  • X is O or S
  • R 1 is in each case independently selected from hydrogen, halogen, CN, CrC 6 -alkyl, C 1 -C 6 - halogenalkyl, C 2 -C 6 -alkenyl, C 2 -C 6 -halogenalkenyl, C 2 -C 6 -alkynyl, C 2 -C 6 -halogenalkynyl, 0-CrC 6 -alkyl, 0-C 2 -C 6 -alkenyl, 0-C 2 -C 6 -alkynyl, C 3 -C 6 -cycloalkyl, wherein the acyclic and cyclic moieties of R 1 are unsubstituted or substituted by one to six groups R 1a which independently of one another are selected from:
  • halogen CN, CrC 6 -alkyl, CrC 6 -halogenalkyl, C 2 -C 6 -alkenyl, C 2 -C 6 -halogenalkenyl, C 2 -C 6 - alkynyl, C 2 -C 6 -halogenalkynyl, 0-CrC 6 -alkyl, 0-C 2 -C 6 -alkenyl, 0-C 2 -C 6 -alkynyl;
  • R 2 is in each case independently selected from halogen, CN, CrC 6 -alkyl, CrC 6 -halogenalkyl, C 2 -C 6 -alkenyl, C 2 -C 6 -halogenalkenyl, C 2 -C 6 -alkynyl, C 2 -C 6 -halogenalkynyl, 0-CrC 6 -alkyl, 0-C 2 -C 6 -alkenyl, 0-C 2 -C 6 -alkynyl, C 3 -C 6 -cycloalkyl, wherein the acyclic and cyclic moieties of R 2 are unsubstituted or substituted by one to six groups R 2a which independently of one another are selected from:
  • halogen CN, CrC 6 -alkyl, CrC 6 -halogenalkyl, C 2 -C 6 -alkenyl, C 2 -C 6 -halogenalkenyl, C 2 -C 6 - alkynyl, C 2 -C 6 -halogenalkynyl, 0-CrC 6 -alkyl, 0-C 2 -C 6 -alkenyl, 0-C 2 -C 6 -alkynyl;
  • R 3 is in each case independently selected from halogen, CN, CrC 6 -alkyl, CrC 6 -halogenalkyl, C 2 -C 6 -alkenyl, C 2 -C 6 -halogenalkenyl, C 2 -C 6 -alkynyl, C 2 -C 6 -halogenalkynyl, 0-CrC 6 -alkyl, 0-C 2 -C 6 -alkenyl, 0-C 2 -C 6 -alkynyl, C 3 -C 6 -cycloalkyl, wherein the acyclic and cyclic moieties of R 3 are unsubstituted or substituted by one to six groups R 3a which independently of one another are selected from: halogen, CN, CrC 6 -alkyl, CrC 6 -halogenalkyl, C 2 -C 6 -alkenyl, C 2 -C 6 -halogenalkenyl, C 2 -
  • R 4 is in each case independently selected from hydrogen, halogen, CN, Ci-C 6 -alkyl, C 1 -C 6 - halogenalkyl, C 2 -C 6 -alkenyl, C 2 -C 6 -halogenalkenyl, C 2 -C 6 -alkynyl, C 2 -C 6 -halogenalkynyl, 0-Ci-C 6 -alkyl, 0-C 2 -C 6 -alkenyl, 0-C 2 -C 6 -alkynyl, C 3 -C 6 -cycloalkyl, wherein the acyclic and cyclic moieties of R 4 are unsubstituted or substituted by one to six groups R 4a which independently of one another are selected from:
  • halogen CN, Ci-C 6 -alkyl, Ci-C 6 -halogenalkyl, C 2 -C 6 -alkenyl, C 2 -C 6 -halogenalkenyl, C 2 -C 6 - alkynyl, C 2 -C 6 -halogenalkynyl, 0-Ci-C 6 -alkyl, 0-C 2 -C 6 -alkenyl, 0-C 2 -C 6 -alkynyl;
  • A is direct bond or C(R 7 R 8 );
  • ⁇ are in each case independently selected from hydrogen, halogen, CN, Ci-C 6 -alkyl, C 1 -C 6 - halogenalkyl, C 2 -C 6 -alkenyl, C 2 -C 6 -halogenalkenyl, C 2 -C 6 -alkynyl, C 2 -C 6 -halogenalkynyl, O-CrCe-alkyl, 0-C 2 -C 6 -alkenyl, 0-C 2 -Ce-alkynyl, Cs-Ce-cycloalkyl, O-Cs-Ce-cycloalkyl, CH 2 -C 3 -C 6 -cycloalkyl, C 3 -C 6 -cycloalkenyl, 0-C 3 -C 6 -cycloalkenyl, CH 2 -C 3 -C 6 -cycloalkenyl, wherein the acyclic moieties of R 5 , R 6
  • R ' is as defined above;
  • R 5 , R 6 , R 7 or R 8 can not all be H
  • R 9 when A is C(R 7 R 8 ) R 9 can be also H;
  • the N-oxides may be prepared from the inventive compounds according to conventional oxidation methods, e. g. by treating compounds I with an organic peracid such as
  • metachloroperbenzoic acid cf. WO 03/64572 or J. Med. Chem. 38(11), 1892-903, 1995
  • inorganic oxidizing agents such as hydrogen peroxide (cf. J. Heterocyc. Chem. 18(7), 1305-8, 1981) or oxone (cf. J. Am. Chem. Soc. 123(25), 5962-5973, 2001).
  • the oxidation may lead to pure mono-N-oxides or to a mixture of different N-oxides, which can be separated by conventional methods such as chromatography.
  • Agriculturally acceptable salts of the compounds of the formula I encompass especially the salts of those cations or the acid addition salts of those acids whose cations and anions, respectively, have no adverse effect on the fungicidal action of the compounds I.
  • Suitable cations are thus in particular the ions of the alkali metals, preferably sodium and potassium, of the alkaline earth metals, preferably calcium, magnesium and barium, of the transition metals, preferably manganese, copper, zinc and iron, and also the ammonium ion which, if desired, may be substituted with one to four CrC4-alkyl substituents and/or one phenyl or benzyl substituent, preferably diisopropylammonium, tetramethylammonium, tetrabutylammonium,
  • trimethylbenzylammonium furthermore phosphonium ions, sulfonium ions, preferably tri(Ci-C4- alkyl)sulfonium, and sulfoxonium ions, preferably tri(Ci-C4-alkyl)sulfoxonium.
  • Anions of acceptable acid addition salts are primarily chloride, bromide, fluoride,
  • Ci-C4-alkanoic acids preferably formate, acetate, propionate and butyrate. They can be formed by reacting a compound I with an acid of the corresponding anion, preferably of hydrochloric acid, hydrobromic acid, sulfuric acid, phosphoric acid or nitric acid.
  • Stereoisomers of the formula I can exist as one or more stereoisomers.
  • the various stereoisomers include enantiomers, diastereomers, atropisomers arising from restricted rotation about a single bond of asymmetric groups and geometric isomers. They also form part of the subject matter of the present invention.
  • one stereoisomer may be more active and/or may exhibit beneficial effects when enriched relative to the other stereoisomer(s) or when separated from the other stereoisomer(s). Additionally, the skilled artisan knows how to separate, enrich, and/or to selectively prepare said stereoisomers.
  • the compounds of the invention may be present as a mixture of stereoisomers, e.g. a racemate, individual
  • C n -C m indicates the number of carbon atoms possible in each case in the substituent or substituent moiety in question.
  • halogen refers to fluorine, chlorine, bromine and iodine.
  • CrC 6 -alkyl refers to a straight-chained or branched saturated hydrocarbon group having 1 to 6 carbon atoms, e.g. methyl, ethyl, propyl, 1-methylethyl, butyl, 1-methylpropyl, 2- methylpropyl, 1 , 1 -di methylethyl , pentyl, 1-methylbutyl, 2-methylbutyl, 3-methylbutyl,
  • C2-C4-alkyl refers to a straight-chained or branched alkyl group having 2 to 4 carbon atoms, such as ethyl, propyl (n-propyl), 1-methylethyl (iso-propoyl), butyl, 1-methylpropyl (sec.-butyl), 2-methylpropyl (iso-butyl), 1 , 1 -dimethylethyl (tert.-butyl).
  • Ci-C 6 -halogenalkyl refers to an alkyl group having 1 or 6 carbon atoms as defined above, wherein some or all of the hydrogen atoms in these groups may be replaced by halogen atoms as mentioned above.
  • Ci-C2-halogenalkyl such as chloromethyl, bromomethyl, dichloromethyl, trichloromethyl, fluoromethyl, difluoromethyl, trifluoromethyl, chlorofluoromethyl, dichlorofluoromethyl, chlorodifluoromethyl, 1-chloroethyl, 1-bromoethyl, 1- fluoroethyl, 2-fluoroethyl, 2,2-difluoroethyl, 2,2,2-trifluoroethyl, 2-chloro-2-fluoroethyl, 2-chloro- 2,2-difluoroethyl, 2,2-dichloro-2-fluoroethyl, 2,2,2-trichloroethyl or pentafluoroethyl.
  • CrC 6 -alkoxy refers to a straight-chain or branched alkyl group having 1 to 6 carbon atoms which is bonded via an oxygen, at any position in the alkyl group.
  • Examples are “C1-C4- alkoxy” groups, such as methoxy, ethoxy, n-propoxy, 1-methylethoxy, butoxy, 1-methyhprop- oxy, 2-methylpropoxy or 1 ,1-dimethylethoxy.
  • CrC 6 -halogenalkoxy refers to a CrC 6 -alkoxy radical as defined above, wherein some or all of the hydrogen atoms in these groups may be replaced by halogen atoms as mentioned above.
  • Examples are "CrC4-halogenalkoxy” groups, such as OCH2F, OCHF2, OCF 3 , OCH2CI, OCHCI2, OCCI 3 , chlorofluoromethoxy, dichlorofluoromethoxy, chlorodifluoromethoxy, 2-fluoroethoxy, 2-chlorothoxy, 2-bromoethoxy, 2-iodoethoxy, 2,2-difluoroethoxy, 2,2,2- trifluoroethoxy, 2-chloro-2-fluoroethoxy, 2-chloro-2,2-difluoroethoxy, 2,2-dichloro-2-fluoroethoxy, 2,2,2-trichloroethoxy, OC2F5, 2-fluoropropoxy
  • C2-C6-alkenyl refers to a straight-chain or branched unsaturated hydrocarbon radical having 2 to 6 carbon atoms and a double bond in any position.
  • Examples are “C2-C4-alkenyl” groups, such as ethenyl, 1-propenyl, 2-propenyl (allyl), 1-methylethenyl, 1-butenyl, 2-butenyl, 3-butenyl, 1 -methyl-1 -propenyl, 2-methyl-1-propenyl, 1-methyl-2-propenyl, 2-methyl-2-propenyl.
  • C2-C6-halogenalkenyl refers to an alkyl group having 2 or 6 carbon atoms as defined above, wherein some or all of the hydrogen atoms in these groups may be replaced by halogen atoms as mentioned above.
  • C2-C6-alkenyloxy refers to a straight-chain or branched alkenyl group having 2 to 6 carbon atoms which is bonded via an oxygen, at any position in the alkenyl group. Examples are “C2-C4-alkenyloxy” groups.
  • C2-C6-alkynyl refers to a straight-chain or branched unsaturated hydrocarbon radical having 2 to 6 carbon atoms and containing at least one triple bond.
  • Examples are "C2-C4- alkynyl” groups, such as ethynyl, prop-1-ynyl, prop-2-ynyl (propargyl), but-1-ynyl, but-2-ynyl, but-3-ynyl , 1 -methyl-prop-2-ynyl .
  • C2-C6-halogenalkynyl refers to an alkyl group having 2 or 6 carbon atoms as defined above, wherein some or all of the hydrogen atoms in these groups may be replaced by halogen atoms as mentioned above.
  • C2-C6-alkynyloxy refers to a straight-chain or branched alkynyl group having 2 to 6 carbon atoms which is bonded via an oxygen, at any position in the alkynyl group. Examples are “C2-C4-alkynyloxy” groups.
  • C3-C6-cycloalkyl refers to monocyclic saturated hydrocarbon radicals having 3 to 6 carbon ring members, such as cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl. Accordingly, a saturated three-, four-, five-, six-, seven-, eight-, nine or ten-membered carbocyclyl or carbo- cycle is a "C3-Cio-cycloalkyl".
  • C3-C6-cycloalkenyl refers to a monocyclic partially unsaturated 3-, 4- 5- or 6- membered carbocycle having 3 to 6 carbon ring members and at least one double bond, such as cyclopentenyl, cyclopentadienyl, cyclohexadienyl. Accordingly, a partially unsaturated three-, four-, five-, six-, seven-, eight-, nine or ten-membered carbocyclyl or carbocycle is a "C3-C10- cycloalkenyl".
  • C3-C8-cycloalkyl-Ci-C4-alkyl refers to alkyl having 1 to 4 carbon atoms (as defined above), whereAccording to one hydrogen atom of the alkyl radical is replaced by a cycloalkyl radical having 3 to 8 carbon atoms (as defined above).
  • heterocyclyl or heterocycle contains 1 , 2, 3 or 4 heteroatoms selected from N, O and S
  • the ring member atoms of the heterocycle include besides carbon atoms 1 , 2, 3 or 4 heteroatoms independently selected from the group of O, N and S.
  • a 3- or 4-membered saturated heterocycle which contains 1 or 2 heteroatoms from the group consisting of O, N and S as ring members such as oxirane, aziridine, thiirane, oxetane, azetidine, thiethane, [1 ,2]dioxetane, [1 ,2]dithietane, [1 ,2]diazetidine; and
  • a 5- or 6-membered saturated or partially unsaturated heterocycle which contains 1 , 2 or 3 heteroatoms from the group consisting of O, N and S as ring members such as 2- tetrahydrofuranyl, 3-tetrahydrofuranyl, 2-tetrahydrothienyl, 3-tetrahydrothienyl, 2-pyrrolidinyl, 3- pyrrolidinyl, 3-isoxazolidinyl, 4-isoxazolidinyl, 5-isoxazolidinyl, 3-isothiazolidinyl,
  • hexahydroazepinyl such as 2,3,4,5-tetrahydro[1 H]azepin-1-,-2-,-3-,-4-,-5-,-6- or-7-yl, 3, 4, 5, 6- tetrahydro[2H]azepin-2-,-3-,-4-,-5-,-6- or-7-yl, 2,3,4,7-tetrahydro[1 H]azepin-1-,-2-,-3-,-4-,-5-,-6- or-7-yl, 2,3,6,7-tetrahydro[1 H]azepin-1-,-2-,-3-,-4-,-5-,-6- or-7-yl, hexahydroazepin-1-,-2-,-3- or-yl,
  • substituted refers to substitued with 1 , 2, 3 or up to the maximum possible number of substituents.
  • the term“5-or 6-membered heteroaryl” or“5-or 6-membered heteroaromatic” refers to aromatic ring systems incuding besides carbon atoms, 1 , 2, 3 or 4 heteroatoms independently selected from the group consisting of N, O and S, for example, a 5-membered heteroaryl such as pyrrol-1 -yl, pyrrol-2-yl, pyrrol-3-yl, thien-2-yl, thien-3-yl, furan- 2-yl, furan-3-yl, pyrazol-1-yl, pyrazol-3-yl, pyrazol-4-yl, pyrazol-5-yl, imidazol-1-yl, imidazol-2-yl, imidazol-4-yl, imidazol-5-yl, oxazol-2-yl, oxazol-4-yl, oxazol-5-yl, isoxazol-3-yl, isox
  • a 6-membered heteroaryl such as pyridin-2-yl, pyridin-3-yl, pyridin-4-yl, pyridazin-3-yl, pyridazin-4-yl, pyrimidin-2-yl, pyrimidin-4-yl, pyrimidin-5-yl, pyrazin-2-yl and 1 ,3,5-triazin-2-yl and
  • R 1 is H, halogen, Ci-C 6 -alkyl or Ci-C 6 -halogenalkyl, in particular H, F, Cl, CH 3 , C2H5, CF 3 more specifically H, CH 3 , F or Cl most preferred H, F or Cl, especially R 1 is hydrogen.
  • R 1 Particularly preferred embodiments of R 1 according to the invention are in Table P1 below, wherein each line of lines P1-1 to P1-13 corresponds to one particular embodiment of the invention. Thereby, for every R 1 that is present in the inventive compounds, these specific embodiments and preferences apply independently of the meaning of any other R 1 that may be present in the ring:
  • R 2 is selected from the group consisting of C 1 -C 6 - alkyl, CrC 6 -halogenalkyl, 0-CrC 6 -alkyl, C 3 -C 6 -cycloalkyl, in particular CH 3 , C 2 H 5 , CF 3 , CH 2 F, CHF 2 , OCH 3 , OC 2 H 5 , O-C 3 H 7 , O-C 4 H 9 , cyclopropyl, cyclobutyl, more specifically CH 3 , CH 2 F, CF 2 H, CF 3 , OCH3, OC2H5, most preferred OCH 3 , CH 3 .
  • R 2 is halogen, in particular F, Cl, Br or I, more specifically F, Cl or Br, in particular F or Cl.
  • R 2 is F.
  • R 2 is Cl
  • R 2 is Br
  • R 2 is CrC6-alkyl, in particular CrC 4 -alkyl, such as CH 3 . or C 2 H 5 , in particular CH 3 or CH 2 CH 3 .
  • R 2 is CrC6-halogenalkyl, in particular C 1 -C 4 - halogenalkyl, such as CF 3 , CCI 3 , FCH 2 , CICH 2 , F 2 CH, CI 2 CH, CF3CH2, CCI3CH2 or CF 2 CHF 2 .
  • R 2 is C 2 -C 6 -alkynyl or C 2 -C 6 -halogenalkynyl, in particular C 2 -C 4 -alkynyl or C 2 -C 4 -halogenalkynyl, such as CECH, CFhCECH, CECCI,
  • R 2 is 0-CrC 6 -alkyl, in particular C 1 -C 4 - alkyl, more specifically Ci-C 2 -alkoxy.
  • R 2 is such as OCH 3 or OCH 2 CH 3 .
  • R 2 is 0-CrC6-alkyl
  • R 2 is 0-C2-C6-alkenyl in particular C 2 - C 4 -alkenyl, more specifically C 2 -C 3 -alkenyl.
  • R 2 is 0-C2-C6-alkynyl, in particular C 2 - C6-alkynyl, in particular C 2 -C 4 -alkynyl, more specifically C 2 -C 3 -alkynyl.
  • R 2 is such as O-CH 2 - CECH.
  • R 2 is 0-CrC6-halogenalkyl, in particular OCF3, OCC , OFCH2, OCICH2, OF2CH, OCI2CH, OCF3CH2, OCCI3CH2 or OCF2CHF2, more specifically OCF 3 , OF 2 CH, OFCH 2.
  • R 2 is C 3 -C 6 -cycloalkyl, in particular cyclopropyl or cyclobutyl.
  • R 2 is C 3 -C 6 -halogencycloalkyl.
  • R 2 is fully or partially halogenated cyclopropyl, such as 1-F-cyclopropyl, 1-CI- cyclopropyl, 2,2-F2-cyclopropyl, 2,2-Cl2-cyclopropyl .
  • R 2 Particularly preferred embodiments of R 2 according to the invention are in Table P2 below, wherein each line of lines P2- 1 to P2-21 corresponds to one particular embodiment of the invention, wherein P2- 1 to P2-21 are also in any combination with one another a preferred embodiment of the present invention.
  • the connection point to the carbon atom, to which R 2 is bound is marked with“#” in the drawings.
  • R 3 is selected from the group consisting of C 1 -C 6 - alkyl, CrC 6 -halogenalkyl, 0-CrC 6 -alkyl, C 3 -C 6 -cycloalkyl, in particular CH 3 , C 2 H 5 , CF 3 , CH 2 F, CHF 2 , OCH 3 , OC 2 H 5 , O-C 3 H 7 , O-C 4 H 9 , cyclopropyl, cyclobutyl, more specifically CH 3 , CH 2 F, CF2H, CF3, cyclopropyl, cyclobutyl, most preferred CH3, CF2H, CF3.
  • R 3 is halogen, in particular F, Cl, Br or I, more specifically F, Cl or Br, in particular F or Cl.
  • R 3 is F.
  • R 3 is Cl
  • R 3 is Br.
  • R 3 is CrC6-alkyl, in particular CrC 4 -alkyl, such as CH3 or C2H5, in particular CH3 or CH2CH3.
  • R 3 is CrC6-halogenalkyl, in particular C1-C4- halogenalkyl, such as CF 3 , CCI 3 , FCH 2 , CICH 2 , F 2 CH, CI 2 CH, CF3CH2, CCI3CH2 or CF 2 CHF 2 .
  • R 3 is C2-C6-alkynyl or C2-C6-halogenalkynyl, in particular C2-C4-alkynyl or C2-C4-halogenalkynyl, such as CECH, ChhCECH, CECCI,
  • R 3 is 0-CrC 6 -alkyl, in particular C1-C4- alkyl, more specifically Ci-C 2 -alkoxy.
  • R 3 is such as OCH 3 or OCH 2 CH 3 .
  • R 3 is 0-C 2 -C 6 -alkenyl in particular C2- C4-alkenyl, more specifically C2-C3-alkenyl.
  • R 3 is 0-C 2 -C 6 -alkynyl, in particular C2- C 6 -alkynyl, in particular C2-C4-alkynyl, more specifically C2-C3-alkynyl.
  • R 3 is such as O-CH2- CECH.
  • R 3 is 0-CrC 6 -halogenalkyl, in particular OCF3, OCC , OFCH2, OCICH2, OF2CH, OCI2CH, OCF3CH2, OCCI3CH2 or OCF2CHF2, more specifically OCF 3 , OF 2 CH, OFCH 2 .
  • R 3 is C3-C6-cycloalkyl, in particular cyclopropyl, cyclobutyl.
  • R 3 is C3-C6-halogencycloalkyl.
  • R 3 is fully or partially halogenated cyclopropyl, such as 1-F-cyclopropyl, 1-CI- cyclopropyl, 2,2-F 2 -cyclopropyl, 2,2-Cl 2 -cyclopropyl .
  • R 3 Particularly preferred embodiments of R 3 according to the invention are in Table P3 below, wherein each line of lines P3-1 to P3-21 corresponds to one particular embodiment of the invention, wherein P3-1 to P3-21 are also in any combination with one another a preferred embodiment of the present invention.
  • the connection point to the carbon atom, to which R 3 is bound is marked with“#” in the drawings.
  • R 4 is H, halogen, CrC 6 -alkyl or CrC 6 -halogenalkyl, in particular H, F, Cl, CH 3 , C2H5, CF 3 more specifically H, CH 3 , F or Cl most preferred H, F or Cl, especially R 4 is hydrogen.
  • R 4 Particularly preferred embodiments of R 4 according to the invention are in Table P4 below, wherein each line of lines P4-1 to P4-10 corresponds to one particular embodiment of the invention. Thereby, for every R 4 that is present in the inventive compounds, these specific embodiments and preferences apply independently of the meaning of any other R 4 that may be present in the ring:
  • ⁇ are in each case independently selected from hydrogen, halogen, CN, CrC 6 -alkyl, C 1 -C 6 - halogenalkyl, C 2 -C 6 -alkenyl, C 2 -C 6 -halogenalkenyl, C 2 -C 6 -alkynyl, C 2 -C 6 -halogenalkynyl, O-CrCe-alkyl, 0-C 2 -Ce-alkenyl, 0-C 2 -Ce-alkynyl, C 3 -Ce-cycloalkyl, 0-C 3 -Ce-cycloalkyl, CH 2 -C 3 -C 6 -cycloalkyl, C 3 -C 6 -cycloalkenyl, 0-C 3 -C 6 -cycloalkenyl, CH 2 -C 3 -C 6 -cycloalkenyl, wherein the acyclic moieties of R 5 , R 6
  • R 5 , R 6 , R 7 , R 8 are in each case independently selected from H, halogen, CN, CrC 6 -alkyl, CrC 6 -halogenalkyl, C 2 -C 6 -alkenyl, C 2 -C 6 -halogenalkenyl, 0-CrC 6 -alkyl, C 3 -C 6 -cycloalkyl, 0-C 3 -C 6 -cycloalkyl, CH 2 -C 3 -C 6 -cycloalkyl, C 3 - C 6 -cycloalkenyl, 0-C 3 -C 6 -cycloalkenyl, CH 2 -C 3 -C 6 -cycloalkenyl.
  • R 5 is preferably H, CrC 6 -alkyl or CrC 6 -alkyl-0-Ci-C 6 -alkyl, more preferably H, CH 3, CH 2 OCH 3 .
  • R 6 is preferably CrC 6 -alkyl, C 1 -C 4 - halogenalkyl, C 2 -C 4 -alkenyl, 0-CrC 6 -alkyl, C 2 -C 4 -halogenalkenyl, cyclopropyl, CFh-cyclopropyl.
  • R 7 is preferably H or CrC 6 -alkyl, more preferably H and CH 3 .
  • R 8 is preferably H or CrC 6 -alkyl, more preferably H and CH 3 .
  • R 5 , R 6 , R 7 , R 8 are in each case independently H. According to still another embodiment of formula I, R 5 , R 6 , R 7 , R 8 are in each case independently halogen, preferably F or Cl, most preferably F.
  • R 5 , R 6 , R 7 , R 8 are in each case independently CN.
  • R 5 , R 6 , R 7 , R 8 are in each case
  • CrC 6 -alkyl such as CH 3 , C 2 H 5 , n-propyl, i-propyl, n-butyl, i-butyl, tert-butyl, n- pentyl, i-pentyl or CH 2 -C(CH 3 ) 3 .
  • R 5 , R 6 , R 7 , R 8 are in each case
  • CrC 6 -halogenalkyl in particular CrC 4 -halogenalkyl, such as CF 3 , CC , FCH 2 , CICH2, F 2 CH, CI2CH, CF3CH2, CCI3CH2 or CF2CHF2.
  • R 5 , R 6 , R 7 , R 8 are in each case
  • R 5 , R 6 , R 7 , R 8 are in each case
  • C 2 -C 6 -alkynyl or C 2 -C 6 -halogenalkynyl in particular C 2 -C 4 -alkynyl or C 2 -C 4 - halogenalkynyl, such as CECH, CFhCECH, CECCI, CFhCECCI, or CC CECCI.
  • R 5 , R 6 , R 7 , R 8 are in each case independently 0-Ci-C 6 -alkanyl.
  • R 5 , R 6 , R 7 , R 8 are in each case independently such as OCH 3 , OC 2 H 5 , O-n-propyl, O-iso-propyl, O-i-butyl, O-tert-butyl or 0-CH 2 -C(CH 3 ) 3 .
  • R 5 , R 6 , R 7 , R 8 are in each case independently C 3 -C 6 -cycloalkyl, 0-C 3 -C 6 -cycloalkyl, CH 2 -C 3 -C 6 -cycloalkyl, C 3 -C 6 -cycloalkenyl, 0-C 3 -C 6 -cycloalkenyl, CH 2 -C 3 -C 6 -cycloalkenyl, wherein C 3 -C 6 -cycloalkyl is preferably selected from the group of cyclopropyl, 1-F-cyclopropyl, 1-CI-cyclopropyl, 2,2-F 2 -cyclopropyl, 2.2-CI 2 - cyclopropyl and cyclohexyl; and wherein C 3 -C 6 -cycloalkenyl is selected from the group of cyclohexen-1-yl, cyclohexen-2-yl
  • R 5 , R 6 , R 7 , R 8 are in each case independently 0-C 2 -C 6 -alkenyl in particular C 2 -C 4 -alkenyl, more specifically C 2 -C 3 -alkenyl.
  • R 5 , R 6 , R 7 , R 8 are in each case independently 0-C 2 -C 6 -alkenyl in particular C 2 -C 4 -alkenyl, more specifically C 2 -C 3 -alkenyl.
  • R 5 , R 6 , R 7 , R 8 are in each case independently 0-C 2 -C 6 -alkynyl, in particular C 2 -C 6 -alkynyl, in particular C 2 -C 4 -alkynyl, more specifically C 2 -C 3 -alkynyl.
  • R 5 , R 6 , R 7 , R 8 are in each case independently such as OCFhCECH.
  • R 5 , R 6 , R 7 , R 8 are in Table P5 below, wherein each line of lines P5-1 to P5-30 corresponds to one particular embodiment of the invention, wherein P5-1 to P5-30 are also in any combination with one another a preferred embodiment of the present invention.
  • the connection point to the carbon atom, to which R 5 is bound is marked with“#” in the drawings.
  • R 9 is selected from the group consisting of CH 3 , CH2CH3, CH(CH 3 )2, CH(CH 3 )3, CF 3 , CF(CH 3 )2, CH 2 OCH(CH 3 )2, cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, C 6 H 5 , 4-F-C 6 H 4 ; most preferred CH 3 and phenyl.
  • R 9 is CrC 6 -alkyl, in particular CrC4-alkyl, such as CH 3 or C2H5, in particular CH 3 or CH2CH 3 .
  • R 9 is CrC 6 -halogenalkyl, in particular C1 -C4- halogenalkyl, such as CF 3 , CC , FCH 2 , CICH 2 , F 2 CH, CI 2 CH, CF 3 CH 2 , CCI 3 CH 2 or CF 2 CHF 2 .
  • R 9 is C 2 -C 6 -alkynyl or C 2 -C 6 -halogenalkynyl, in particular C 2 -C4-alkynyl or C 2 -C4-halogenalkynyl, such as CECH, CH 2 CECH, CECCI,
  • R 9 is C 3 -C 6 -cycloalkyl, in particular cyclopropyl, cyclohexyl.
  • R 9 is C 3 -C 6 -cycloalkenyl, in particular cyclopentenyl, or cyclohexenyl.
  • R 9 is phenyl, wherein phenyl in each case is unsubstituted or substituted by identical or different groups R 9a which independently of one another are selected from halogen, CrC 2 -alkyl, CN.
  • R 9 is a 5-membered heteroaryl such as pyrrol-1 -yl, pyrrol-2-yl, pyrrol-3-yl, thien-2-yl, thien-3-yl, furan-2-yl, furan-3-yl, pyrazol-1-yl, pyrazol-3-yl, pyrazol-4-yl, pyrazol-5-yl, imidazol-1-yl, imidazol-2-yl, imidazol-4-yl, imidazol-5-yl, oxazol-2-yl, oxazol4-yl, oxazol-5-yl, isoxazol-3-yl, isoxazol-4-yl, isoxazol-5-yl, thiazol-2-yl, thiazol-4-yl, thiazol-5-yl, isothiazol-3-yl, isothiazol-4-yl, isothiazol-4
  • 1.2.4-thiadiazol-5-yl preferred are pyrazol-1-yl, pyrazol-3-yl, pyrazol-4-yl, pyrazol-5-yl,
  • R 9 is a 6-membered heteroaryl such as pyridin-2-yl, pyridin-3-yl, pyridin-4-yl, pyridazin-3-yl, pyridazin-4-yl, pyrimidin-2-yl, pyrimidin-4-yl, pyrimidin-5-yl, pyrazin-2-yl and 1 ,3,5-triazin-2-yl and 1 ,2,4-triazin-3-yl, preferred are pyridin-2-yl, pyridin-3-yl, pyridin-4-yl.
  • the 6-membered heteroaryl in each case is unsubstituted or substituted by identical or different groups R 9a which independently of one another are selected from halogen, Ci-C 2 -alkyl, CN.
  • R 9 Particularly preferred embodiments of R 9 according to the invention are in Table P9 below, wherein each line of lines P9-1 to P9-104 corresponds to one particular embodiment of the invention, wherein P5-1 to P5-104 are also in any combination with one another a preferred embodiment of the present invention.
  • the connection point to the carbon atom, to which R 9 is bound is marked with“#” in the drawings.
  • the invention relates to compounds of the formula I, or the N-oxides, or the agriculturally acceptable salts thereof, wherein
  • X is O; A is C(R 7 R 8 );
  • R 1 is H
  • R 2 is selected from the group consisting of CrC 6 -alkyl, CrC 6 -halogenalkyl or 0-CrC 6 -alkyl
  • R 3 is selected from the group consisting of CrC 6 -alkyl, CrC 6 -halogenalkyl or C3-C4-cycloalkyl
  • R 4 is H
  • the invention relates to compounds of the formula I, or the N-oxides, or the agriculturally acceptable salts thereof, wherein
  • X is O
  • A is C(R 7 R 8 );
  • R 1 is H
  • R 2 is selected from the group consisting of CH 3 , C2H5, CF 3 , CH2F, CHF2, OCH 3 , OC2H5, O-C 3 H7, O-C4H 9 , cyclopropyl, cyclobutyl;
  • R 3 is selected from the group consisting of CH 3 , C2H5, CF 3 , CH2F, CHF2, cyclopropyl, cyclobutyl;
  • R 4 is H;
  • R 5 , R 6 , R 7 , R 8 are independently selected from H, halogen, CN, CrC 6 -alkyl, CrC 6 -halogenalkyl, C3-C6-cycloalkyl, 0-CrC 6 -alkyl, or two moieties:
  • the invention relates to compounds of the formula I, or the N-oxides, or the agriculturally acceptable salts thereof, wherein
  • X is O
  • A is C(R 7 R 8 );
  • R 1 is H
  • R 2 is selected from the group consisting of CH 3 , OCH 3 ;
  • R 3 is selected from the group consisting of CH 3 , CF 3 , CF2H;
  • R 4 is H
  • R 5 is selected from the group consisting of H, F, Cl, CN, CH 3, CH2OCH 3 .
  • R 6 is selected from the group consisting of CrC 6 -alkyl, CrC4-halogenalkyl, C2-C4-alkenyl, C2-C4- halogenalkenyl, cyclopropyl, CFh-cyclopropyl,
  • R 7 is selected from the group consisting of H and CH 3 ;
  • R 8 is selected from the group consisting of H and CH 3 .
  • R 9 is selected from the group consisting of CH 3 , phenyl, pyridine-2-yl, pyridine-3-yl, pyridine-4-yl and cyclohexyl.
  • the invention relates to compounds of the formula I, or the N-oxides, or the agriculturally acceptable salts thereof, wherein
  • X is O; A is a direct bond
  • R 1 is H
  • R 2 is selected from the group consisting of CH 3 , OCH 3 ;
  • R 3 is selected from the group consisting of CH 3 , CF 3 , CF2H;
  • R 4 is H
  • R 5 is selected from the group consisting of H, F, Cl, CN, CH 3, CH2OCH 3 .
  • R 6 is selected from the group consisting of CrC 6 -alkyl, CrC4-halogenalkyl, C2-C4-alkenyl, C2-C4- halogenalkenyl, cyclopropyl, CFh-cyclopropyl,
  • R 7 is selected from the group consisting of H and CH 3 ;
  • R 8 is selected from the group consisting of H and CH 3 .
  • R 9 is selected from the group consisting of CH 3 , phenyl, pyridine-2-yl, pyridine-3-yl, pyridine-4-yl and cyclohexyl.
  • the invention relates to compounds of the formula I, or the N-oxides, or the agriculturally acceptable salts thereof, wherein
  • X is O
  • A is a direct bond
  • R 1 is H
  • R 2 is selected from the group consisting of CH 3 , C2H5, CF 3 , CH2F, CHF2, OCH 3 , OC2H5, O-C 3 H7, O-C4H 9 , cyclopropyl, cyclobutyl;
  • R 3 is selected from the group consisting of CH 3 , C2H5, CF 3 , CH2F, CHF2, cyclopropyl, cyclobutyl;
  • R 4 is H;
  • R 5 , R 6 are independently selected from H, halogen, CN, CrC 6 -alkyl, CrC 6 -halogenalkyl, O-C1- C 6 -alkyl, or two moieties:
  • the invention relates to compounds of the formula I, or the N-oxides, or the agriculturally acceptable salts thereof, wherein
  • X is O
  • A is a direct bond
  • R 1 is H
  • R 2 is selected from the group consisting of CH 3 , OCH 3 ;
  • R 3 is selected from the group consisting of CH 3 , CF 3 , CF2H;
  • R 4 is H
  • R 5 is selected from the group consisting of H, CH 3, CH2OCH 3 .
  • R 6 is selected from the group consisting of CrC 6 -alkyl, CrC4-halogenalkyl, C2-C4-alkenyl,
  • R 9 is selected from the group consisting of CH 3 and cyclopropyl.
  • Preferred embodiments of the present invention are the following compounds I.A-1 , I.A-2, I.A-3, I.A-4, I.A-5, I.A-6, I.A-6; compounds I.B-1 , I.B-2, I.B-3, I.B-4, I.B-5, I.B-6.
  • the substituents R 5 , R 6 , R 7 , R 8 and R 9 are independently as defined above or preferably defined herein:
  • Table 1a Compounds of the formula I.A-1, I.A-2, I.A-3, I.A-4, I.A-5, I.A-6; I.B-1, I.B-2, I.B-3, I.B-4, I.B-5, I.B-6 in which A is -CH2- and the meaning for the combination of R 5 , R 6 and R 9 for each individual compound corresponds in each case to one line of Table B (compounds I.A- 1.1a.B-1 to I.A-1.1a.B-396, I.A-2.1a.B-1 to I.A-2.1a.B-396, I.A-3.1a.B-1 to I.A-3.1a.B-396, I.A-
  • Table 2a Compounds of the formula I.A-1, I.A-2, I.A-3, I.A-4, I.A-5, I.A-6; I.B-1, I.B-2, I.B-3, I.B-4, I.B-5, I.B-6 in which A is -CHF- and the meaning for the combination of R 5 , R 6 and R 9 for each individual compound corresponds in each case to one line of Table B (compounds I.A- 1.2a.B-1 to I.A-1.2a.B-396, I.A-2.2a.B-1 to I.A-2.2a.B-396, I.A-3.2a.B-1 to I.A-3.2a.B-396, I.A-
  • Table 3a Compounds of the formula I.A-1 , I.A-2, I.A-3, I.A-4, I.A-5, I.A-6; I.B-1 , I.B-2, I.B-3, I.B-4, I.B-5, I.B-6 in which A is -CH(CH3)- and the meaning for the combination of R 5 , R 6 and R 9 for each individual compound corresponds in each case to one line of Table B (compounds I.A-
  • Table 4a Compounds of the formula I.A-1 , I.A-2, I.A-3, I.A-4, I.A-5, I.A-6; I.B-1 , I.B-2, I.B-3, I.B-4, I.B-5, I.B-6 in which A is -CF(CH3)- and the meaning for the combination of R 5 , R 6 and R 9 for each individual compound corresponds in each case to one line of Table B (compounds I.A-
  • Table 5a Compounds of the formula I.A-1 , I.A-2, I.A-3, I.A-4, I.A-5, I.A-6; I.B-1 , I.B-2, I.B-3, I.B-4, I.B-5, I.B-6 in which A is -CF2- and the meaning for the combination of R 5 , R 6 and R 9 for each individual compound corresponds in each case to one line of Table B (compounds I.A- 1.5a.B-1 to I.A-1.5a. B-396, I.A-2.5a.B-1 to I.A-2.5a.B-396, I.A-3.5a.B-1 to I.A-3.5a.B-396, I.A-
  • Table 6a Compounds of the formula I.A-1 , I.A-2, I.A-3, I.A-4, I.A-5, I.A-6; I.B-1 , I.B-2, I.B-3, I.B-4, I.B-5, I.B-6 in which A is -C(CH3)2- and the meaning for the combination of R 5 , R 6 and R 9 for each individual compound corresponds in each case to one line of Table B (compounds I.A-
  • Table 7a Compounds of the formula I.A-1 , I.A-2, I.A-3, I.A-4, I.A-5, I.A-6; I.B-1 , I.B-2, I.B-3, I.B-4, I.B-5, I.B-6 in which A is direct bound and the meaning for the combination of R 5 , R 6 and R 9 for each individual compound corresponds in each case to one line of Table B (compounds I.A-1.7a.B-1 to I.A-1.7a.B-396, I.A-2.7a.B-1 to I.A-2.7a.B-396, I.A-3.7a.B-1 to I.A-3.7a.B-396, I.A-4.7a.
  • a robust method involves treatment of carboxylic acid of type II I (R 5 -R 9 and A are as defined for compounds of formula I) with an activating agent like phosgene, thionyl chloride or oxalyl chloride or an amide coupling reagent like dicyclohexylcarbodiimide in organic solvent like tetrahydrofuran (THF), dichloromethane (DCM) or dimethylformamide (DMF).
  • an activating agent like phosgene, thionyl chloride or oxalyl chloride
  • an amide coupling reagent like dicyclohexylcarbodiimide in organic solvent like tetrahydrofuran (THF), dichloromethane (DCM) or dimethylformamide (DMF).
  • Compounds of formula (I . A) (wherein X is O and R 1 -R 9 and A are as defined for compounds of formula I) can also be prepared by the amide coupling reaction between 3- aminopyridines of type I I (R 1 -R 4 are as defined for compounds of formula I) and an ester of type IV (R 5 -R 9 and A are as defined for compounds of formula I and Y is Ci - C 6 alkyl or phenyl) in the presence of a Lewis acid such as trimethyl aluminium in an inert organic solvent like toluene under heating as shown in Scheme 2.
  • a Lewis acid such as trimethyl aluminium in an inert organic solvent like toluene under heating as shown in Scheme 2.
  • carboxylic acids of formula (III) (R 5 -R 9 and A are as defined for compounds of formula I) can be prepared from the corresponding esters such as compounds of formula (IV) (R 5 -R 9 and A are as defined for compounds of formula I and Y is Ci - C 6 alkyl or phenyl).
  • esters such as compounds of formula (IV) (R 5 -R 9 and A are as defined for compounds of formula I and Y is Ci - C 6 alkyl or phenyl).
  • alpha functionalization of these esters can be performed by deprotonation with a strong base like lithium
  • carboxylic acids of formula (III) (R 5 -R 9 are as defined for compounds of formula I and A is a bond) can be prepared by various methods that involve functional group transformations, such as a triple bond can be obtained from an aldehyde using the Bestmann-Ohira reagent as described in J. Org. Chem., 1982, 47, 1837-1845).
  • Other new methods for the preparation of carboxylic acids of formula (III) (R 5 -R 9 are as defined for compounds of formula I and A is a bond) are described in literatures (see:
  • N-oxides may be prepared from the inventive compounds according to conventional oxidation methods as described in WO 03/64572 or J. Med. Chem. 1995,1892-903 or J.
  • the compounds I and the compositions according to the invention are particularly important in the control of a multitude of phytopathogenic fungi on various cultivated plants, such as cereals, e. g. wheat, rye, barley, triticale, oats or rice; beet, e. g. sugar beet or fodder beet; fruits, such as pomes, stone fruits or soft fruits, e. g.
  • compounds I and compositions thereof are used for controlling a multitude of fungi on field crops, such as potatoes sugar beets, tobacco, wheat, rye, barley, oats, rice, corn, cotton, soybeans, rape, legumes, sunflowers, coffee or sugar cane; fruits; vines; ornamentals; or vegetables, such as cucumbers, tomatoes, beans or squashes.
  • field crops such as potatoes sugar beets, tobacco, wheat, rye, barley, oats, rice, corn, cotton, soybeans, rape, legumes, sunflowers, coffee or sugar cane; fruits; vines; ornamentals; or vegetables, such as cucumbers, tomatoes, beans or squashes.
  • plant propagation material is to be understood to denote all the generative parts of the plant such as seeds and vegetative plant material such as cuttings and tubers (e. g.
  • potatoes which can be used for the multiplication of the plant. This includes seeds, roots, fruits, tubers, bulbs, rhizomes, shoots, sprouts and other parts of plants, including seedlings and young plants, which are to be transplanted after germination or after emergence from soil.
  • These young plants may also be protected before transplantation by a total or partial treatment by immersion or pouring.
  • treatment of plant propagation materials with compounds I and compositions thereof, respectively is used for controlling a multitude of fungi on cereals, such as wheat, rye, barley and oats; rice, corn, cotton and soybeans.
  • cultiva plants is to be understood as including plants which have been modified by mutagenesis or genetic engineering in order to provide a new trait to a plant or to modify an already present trait.
  • Mutagenesis includes techniques of random mutagenesis using X-rays or mutagenic chemicals, but also techniques of targeted mutagenesis, to create mutations at a specific locus of a plant genome.
  • Targeted mutagenesis techniques frequently use oligonucleotides or proteins like CRISPR/Cas, zinc-finger nucleases, TALENs or meganucleases to achieve the targeting effect.
  • Genetic engineering usually uses recombinant DNA techniques to create modifications in a plant genome which under natural circumstances cannot readily be obtained by cross breeding, mutagenesis or natural recombination.
  • one or more genes are integrated into the genome of a plant to add a trait or improve a trait.
  • transgenic plants These integrated genes are also referred to as transgenes in the art, while plant comprising such transgenes are referred to as transgenic plants.
  • the process of plant transformation usually produces several transformation events, wich differ in the genomic locus in which a transgene has been integrated. Plants comprising a specific transgene on a specific genomic locus are usually described as comprising a specific“event”, which is referred to by a specific event name. Traits which have been introduced in plants or have been modified include herbicide tolerance, insect resistance, increased yield and tolerance to abiotic conditions, like drought.
  • Herbicide tolerance has been created by using mutagenesis as well as using genetic engineering. Plants which have been rendered tolerant to acetolactate synthase (ALS) inhibitor herbicides by mutagenesis and breeding comprise plant varieties commercially available under the name Clearfield®.
  • ALS acetolactate synthase
  • Herbicide tolerance has been created via the use of transgenes to glyphosate, glufosinate, 2,4-D, dicamba, oxynil herbicides, like bromoxynil and ioxynil, sulfonylurea herbicides, ALS inhibitors and 4-hydroxyphenylpyruvate dioxygenase (HPPD) inhibitors, like isoxaflutole and mesotrione.
  • transgenes to glyphosate, glufosinate, 2,4-D, dicamba, oxynil herbicides, like bromoxynil and ioxynil, sulfonylurea herbicides, ALS inhibitors and 4-hydroxyphenylpyruvate dioxygenase (HPPD) inhibitors, like isoxaflutole and mesotrione.
  • HPPD 4-hydroxyphenylpyruvate dioxygenase
  • Transgenes wich have been used to provide herbicide tolerance traits comprise: for tolerance to glyphosate: cp4 epsps, epsps grg23ace5, mepsps, 2mepsps, gat4601 , gat4621 , goxv247; for tolerance to glufosinate: pat and bar, for tolerance to 2,4-D: aad-1 , aad-12; for tolerance to dicamba: dmo; for tolerance to oxynil herbicies: bxn; for tolerance to sulfonylurea herbicides: zm-hra, csr1-2, gm-hra, S4-HrA; for tolerance to ALS inhibitors: csr1-2; and for tolerance to HPPD inhibitors: hppdPF, W336, avhppd-03.
  • Transgenic corn events comprising herbicide tolerance genes include, but are not limited to, DAS40278, MON801 , MON802, MON809, MON810, MON832, MON87411 , MON87419, MON87427, MON88017, MON89034, NK603, GA21 , MZHG0JG, HCEM485, VCO-01981-5, 676, 678, 680, 33121 , 4114, 59122, 98140, Bt10, Bt176, CBH-351 , DBT418, DLL25, MS3,
  • Transgenic soybean events comprising herbicide tolerance genes include, but are not limited to, GTS 40-3-2, MON87705, MON87708, MON87712, MON87769, MON89788, A2704-12, A2704-21 , A5547-127, A5547-35, DP356043, DAS44406-6, DAS68416-4, DAS-81419-2, GU262, SYHT0H2, W62, W98, FG72 and CV127.
  • Transgenic cotton events comprising herbicide tolerance genes include, but are not limited to, 19-51 a, 31707, 42317, 81910, 281-24-236, 3006-210-23, BXN10211 , BXN10215, BXN10222, BXN 10224, MON1445, MON1698, MON88701 , MON88913, GHB119, GHB614, LLCotton25, T303-3 and T304-40.
  • Transgenic canola events comprising herbicide tolerance genes are for example, but not excluding others, MON88302, HCR-1 , HCN10, HCN28, HCN92, MS1 , MS8, PHY14, PHY23, PHY35, PHY36, RF1 , RF2 and RF3.
  • Transgenes which have most frequently been used are toxin genes of Bacillus spp. and synthetic variants thereof, like cry1A, crylAb, cry1Ab-Ac, crylAc, cry1A.105, cry1 F, cry1 Fa2, cry2Ab2, cry2Ae, mcry3A, ecry3.1Ab, cry3Bb1 , cry34Ab1 , cry35Ab1 , cry9C, vip3A(a), vip3Aa20.
  • genes of plant origin such as genes coding for protease inhibitors, like CpTI and pinll, have been transferred to other plants.
  • a further approach uses transgenes such as dvsnf7 to produce double-stranded RNA in plants.
  • Transgenic corn events comprising genes for insecticidal proteins or double stranded RNA include, but are not limited to, Bt10, Bt11 , Bt176, MON801 , MON802, MON809, MON810, MON863, MON87411 , MON88017, MON89034, 33121 , 4114, 5307, 59122, TC1507, TC6275, CBH-351 , MIR162, DBT418 and MZIR098.
  • Transgenic soybean events comprising genes for insecticidal proteins include, but are not limited to, MON87701 , MON87751 and DAS-81419.
  • Transgenic cotton events comprising genes for insecticidal proteins include, but are not limited to, SGK321 , MON531 , MON757, MON1076, MON15985, 31707, 31803, 31807, 31808, 42317, BN LA-601 , Eventl , COT67B, COT102, T303-3, T304-40, GFM Cry1A, GK12, MLS 9124, 281- 24-236, 3006-210-23, GHB119 and SGK321.
  • transgene athb17 being present for example in corn event MON87403, or by using the transgene bbx32, being present for example in the soybean event MON87712.
  • transgenes gm-fad2-1 , Pj.D6D, Nc.Fad3, fad2-1A and fatb1-A. Soybean events comprising at least one of these genes are: 260-05, MON87705 and MON87769.
  • transgene cspB comprised by the corn event MON87460 and by using the transgene Hahb-4, comprised by soybean event IND-00410-5.
  • Preferred combinations of traits are combinations of herbicide tolerance traits to different groups of herbicides, combinations of insect tolerance to different kind of insects, in particular tolerance to lepidopteran and coleopteran insects, combinations of herbicide tolerance with one or several types of insect resistance, combinations of herbicide tolerance with increased yield as well as combinations of herbicide tolerance and tolerance to abiotic conditions.
  • CERA Cera-gmc.org/GMCropDatabase
  • effects which are specific to a cultivated plant comprising a certain gene or event may result in effects which are specific to a cultivated plant comprising a certain gene or event. These effects might involve changes in growth behavior or changed resistance to biotic or abiotic stress factors. Such effects may in particular comprise enhanced yield, enhanced resistance or tolerance to insects, nematodes, fungal, bacterial, mycoplasma, viral or viroid pathogens as well as early vigour, early or delayed ripening, cold or heat tolerance as well as changed amino acid or fatty acid spectrum or content.
  • the compounds I and compositions thereof, respectively, are particularly suitable for controlling the following plant diseases:
  • Albugo spp. white rust on ornamentals, vegetables (e. g. A. Candida ) and sunflowers (e. g. A. tragopogonis ); Alternaria spp. (Alternaria leaf spot) on vegetables (e.g. A. dauci or A. porn), oilseed rape (A. brassicicola or brassicae), sugar beets (A. tenuis), fruits (e.g. A. grandis), rice, soybeans, potatoes and tomatoes (e. g. A. solani, A. grandis or A. alternata), tomatoes (e. g. A. solani or A. alternata) and wheat (e.g. A. triticina) ⁇ , Aphanomyces spp.
  • Ascochyta spp. on cereals and vegetables e. g. A. tritici (anthracnose) on wheat and A. hordei on barley; Aureobasidium zeae (syn. Kapatiella zeae) on corn; Bipolaris and Drechslera spp. (teleomorph: Cochliobolus spp.), e. g. Southern leaf blight (D. maydis) or Northern leaf blight ( B . zeicola) on corn, e. g. spot blotch ( B . sorokiniana) on cereals and e. g.
  • Botrytis cinerea teleomorph: Botryotinia fuckeliana grey mold) on fruits and berries (e. g. strawberries), vegetables (e. g. lettuce, carrots, celery and cabbages); B. squamosa
  • Cochliobolus anamorph: Helminthosporium of Bipolaris
  • spp. leaf spots
  • cereals e. g. C. sativus, anamorph: B. sorokiniana
  • rice e. g. C. miyabeanus, anamorph: H. oryzae
  • Colletotrichum teleomorph: Glomerella
  • spp. anthracnose on cotton (e. g. C. gossypii)
  • corn e. g. C. graminicola: Anthracnose stalk rot
  • soft fruits e. g.
  • beans e. g. C. lindemuthianum
  • soybeans e. g. C. truncatum or C. gloeosporioides
  • vegetables e.g. C. lagenarium or C. capsici
  • fruits e.g. C. acutatum
  • coffee e.g. C. coffeanum or C. kahawae
  • Corticium spp. e. g. C.
  • sasakii sheath blight
  • Corynespora cassiicola leaf spots
  • Cycloconium spp. e. g. C. oleaginum on olive trees
  • Helminthosporium, teleomorph Pyrenophora
  • Phaeomoniella chlamydospora (formerly Phaeoacremonium chlamydosporum)
  • Gibberella spp. on cereals e. g. G. zeae
  • rice e. g. G. fujikuror. Bakanae disease
  • Microdochium (syn. Fusarium) nivale (pink snow mold) on cereals (e. g. wheat or barley);
  • Microsphaera diffusa (powdery mildew) on soybeans; Monilinia spp., e. g. M. laxa, M. fructicola and M. fructigena (syn. Monilia spp.: bloom and twig blight, brown rot) on stone fruits and other rosaceous plants; Mycosphaerella spp. on cereals, bananas, soft fruits and ground nuts, such as e. g. M. graminicola (anamorph: Zymoseptoria tritici formerly Septoria triticr. Septoria blotch) on wheat or M. fijiensis (syn. Pseudocercospora fijiensis ⁇ . black Sigatoka disease) and M.
  • meibomiae (soybean rust) on soybeans; Phialophora spp. e. g. on vines (e. g. P. tracheiphila and P. tetraspora) and soybeans (e. g. P. gregata : stem rot); Phoma lingam (syn. Leptosphaeria biglobosa and L. maculans. root and stem rot) on oilseed rape and cabbage, P. betae (root rot, leaf spot and damping-off) on sugar beets and P. zeae-maydis (syn. Phyllostica zeae) on corn; Phomopsis spp.
  • Plasmodiophora brassicae club root
  • Plasmopara spp. e. g. P. viticola (grapevine downy mildew) on vines and P.
  • Podosphaera spp. (powdery mildew) on rosaceous plants, hop, pome and soft fruits (e. g. P. leucotricha on apples) and curcurbits (P. xanthii ); Polymyxa spp., e. g. on cereals, such as barley and wheat (P. graminis) and sugar beets (P. betae) and thereby transmitted viral diseases; Pseudocercosporella herpotrichoides (syn. Oculimacula yallundae,
  • O. acuformis eyespot, teleomorph: Tapesia yallundae) on cereals, e. g. wheat or barley;
  • Pseudoperonospora downy mildew
  • P. cubensis on cucurbits or P. humili on hop
  • Pseudopezicula tracheiphila red fire disease or .rotbrenneR ' , anamorph
  • Puccinia spp. rusts on various plants, e. g. P. triticina (brown or leaf rust), P. striiformis (stripe or yellow rust), P. hordei (dwarf rust), P. graminis (stem or black rust) or P. recondita (brown or leaf rust) on cereals, such as e. g. wheat, barley or rye, P. kuehnii (orange rust) on sugar cane and P. asparagi on asparagus; Pyrenopeziza spp., e.g. P.
  • R. solani root and stem rot
  • R. solani sheath blight
  • R. cerealis Rhizoctonia spring blight
  • Rhizopus stolonifer black mold, soft rot
  • strawberries carrots, cabbage, vines and tomatoes
  • Rhynchosporium secalis and R. commune scald
  • Sarocladium oryzae and S. attenuatum (sheath rot) on rice
  • Sclerotinia spp. stem rot or white mold
  • vegetables S. minor and S. sclerotiorum
  • field crops such as oilseed rape, sunflowers (e. g. S. sclerotiorum) and soybeans, S. rolfsii (syn.
  • Athelia rolfsii on soybeans, peanut, vegetables, corn, cereals and ornamentals; Septoria spp. on various plants, e. g. S. glycines (brown spot) on soybeans, S. tritici (syn. Zymoseptoria tritici, Septoria blotch) on wheat and S. (syn. Stagonospora) nodorum (Stagonospora blotch) on cereals; Uncinula (syn. Erysiphe) necator ( powdery mildew, anamorph: Oidium tuckeri) on vines; Setosphaeria spp. (leaf blight) on corn (e. g.
  • S. turcicum syn. Helminthosporium turcicum
  • turf Sphacelotheca spp. (smut) on corn, (e. g. S. reiliana, syn. Ustilago reiliana. head smut), sorghum und sugar cane;
  • Sphaerotheca fuliginea (syn. Podosphaera xanthir. powdery mildew) on cucurbits; Spongospora subterranea (powdery scab) on potatoes and thereby transmitted viral diseases; Stagonospora spp. on cereals, e. g. S. nodorum (Stagonospora blotch, teleomorph: Leptosphaeria [syn.
  • phaseoli sugar beets (e. g. U. betae or U. beticola ) and on pulses (e.g. U. vignae, U. pisi, U. viciae-fabae and U. fabae) ⁇ Ustilago spp. (loose smut) on cereals (e. g. U. nuda and U.
  • the compounds I, their mixtures with other active compounds as defined herein and compositions thereof, respectively, are particularly suitable for controlling the following plant diseases: Puccinia spp. (rusts) on various plants, for example, but not limited to P. triticina (brown or leaf rust), P. striiformis (stripe or yellow rust), P. hordei (dwarf rust), P. graminis (stem or black rust) or P. recondita (brown or leaf rust) on cereals, such as e. g. wheat, barley or rye, P. sorghi (common rust) on maize, P. polysora (southern rust) on maize; P.
  • Puccinia spp. rusts
  • rusts rusts
  • P. triticina brown or leaf rust
  • P. striiformis stripe or yellow rust
  • P. hordei dwarf rust
  • coronata e.g. on oats, P. sorghi und P. polysora on corn
  • Puccinia spp. on other crops, e.g. P. heliathi on sunflower, P. arachidis on peanuts
  • Uromyces spp. on pulses and other crops crops, e.g. Uromyces viciae-fabae, Uromyces vigniae, Uromyces pisi, U. ciceris-arietini, U. betae syn U. beticola
  • Phakopsoraceae spp. on various plants, in particular Phakopsora pachyrhizi and P. meibomiae (soybean rust) on soybeans.
  • Fungicide-resistant strains of the above-mentioned phytopathgenic fungi have been reported, with strains resistant to one or more fungicides from various fungicidal mode of action classes being observed including but not limited to beta-tubulin assembly inhibitors, sterol
  • DMI demethylation-inhibitors
  • Qol quinone-outside-inhibitors
  • SDHI succinate dehydrogenase inhibitors
  • the compounds I and compositions thereof, respectively, are also suitable for controlling harmful fungi in the protection of stored products or harvest and in the protection of materials.
  • protection of materials is to be understood to denote the protection of technical and non-living materials, such as adhesives, glues, wood, paper and paperboard, textiles, leather, paint dispersions, plastics, cooling lubricants, fiber or fabrics, against the infestation and destruction by harmful microorganisms, such as fungi and bacteria.
  • Ascomycetes such as Ophiostoma spp., Ceratocystis spp., Aureobasidium pullulans, Sclerophoma spp., Chaetomium spp., Humicola spp., Petriella spp., Trichurus spp.; Basidiomycetes such as Coniophora spp., Coriolus spp., Gloeophyllum spp., Lentinus spp., Pleurotus spp., Poria spp., Serpula spp.
  • yeast fungi are worthy of note: Candida spp. and Saccharomyces cerevisae.
  • the method of treatment according to the invention can also be used in the field of protecting stored products or harvest against attack of fungi and microorganisms.
  • the term "stored products” is understood to denote natural substances of plant or animal origin and their processed forms, which have been taken from the natural life cycle and for which long-term protection is desired.
  • Stored products of crop plant origin such as plants or parts thereof, for example stalks, leafs, tubers, seeds, fruits or grains, can be protected in the freshly harvested state or in processed form, such as pre-dried, moistened, comminuted, ground, pressed or roasted, which process is also known as post-harvest treatment.
  • Also falling under the definition of stored products is timber, whether in the form of crude timber, such as construction timber, electricity pylons and barriers, or in the form of finished articles, such as furniture or objects made from wood.
  • Stored products of animal origin are hides, leather, furs, hairs and the like. The combinations according the present invention can prevent
  • stored products is understood to denote natural substances of plant origin and their processed forms, more preferably fruits and their processed forms, such as pomes, stone fruits, soft fruits and citrus fruits and their processed forms.
  • the compounds I and compositions thereof, respectively, may be used for improving the health of a plant.
  • the invention also relates to a method for improving plant health by treating a plant, its propagation material and/or the locus where the plant is growing or is to grow with an effective amount of compounds I and compositions thereof, respectively.
  • plant health is to be understood to denote a condition of the plant and/or its products which is determined by several indicators alone or in combination with each other such as yield (e. g. increased biomass and/or increased content of valuable ingredients), plant vigor (e. g. improved plant growth and/or greener leaves (“greening effect”)), quality (e. g. improved content or composition of certain ingredients) and tolerance to abiotic and/or biotic stress.
  • yield e. g. increased biomass and/or increased content of valuable ingredients
  • plant vigor e. g. improved plant growth and/or greener leaves (“greening effect”)
  • quality e. g. improved content or composition of certain ingredients
  • tolerance to abiotic and/or biotic stress e. g. improved content or composition of certain ingredients
  • the compounds of formula I can be present in different crystal modifications whose biological activity may differ. They are likewise subject matter of the present invention.
  • the compounds I are employed as such or in form of compositions by treating the fungi or the plants, plant propagation materials, such as seeds, soil, surfaces, materials or rooms to be protected from fungal attack with a fungicidally effective amount of the active substances.
  • the application can be carried out both before and after the infection of the plants, plant propagation materials, such as seeds, soil, surfaces, materials or rooms by the fungi.
  • Plant propagation materials may be treated with compounds I as such or a composition comprising at least one compound I prophylactically either at or before planting or transplanting.
  • the invention also relates to agrochemical compositions comprising an auxiliary and at least one compound I according to the invention.
  • An agrochemical composition comprises a fungicidally effective amount of a compound I.
  • effective amount denotes an amount of the composition or of the compounds I, which is sufficient for controlling harmful fungi on cultivated plants or in the protection of materials and which does not result in a substantial damage to the treated plants. Such an amount can vary in a broad range and is dependent on various factors, such as the fungal species to be controlled, the treated cultivated plant or material, the climatic conditions and the specific compound I used.
  • compositions e. g. solutions, emulsions, suspensions, dusts, powders, pastes, granules, pressings, capsules, and mixtures thereof.
  • composition types are suspensions (e. g. SC, OD, FS), emulsifiable concentrates (e. g. EC), emulsions (e. g. EW, EO, ES, ME), capsules (e. g. CS, ZC), pastes, pastilles, wettable powders or dusts (e. g. WP, SP, WS, DP, DS), pressings (e. g.
  • compositions types are defined in the “Catalogue of pesticide formulation types and international coding system”, Technical
  • compositions are prepared in a known manner, such as described by Mollet and
  • Suitable auxiliaries are solvents, liquid carriers, solid carriers or fillers, surfactants,
  • dispersants dispersants, emulsifiers, wetters, adjuvants, solubilizers, penetration enhancers, protective colloids, adhesion agents, thickeners, humectants, repellents, attractants, feeding stimulants, compatibilizers, bactericides, anti-freezing agents, anti-foaming agents, colorants, tackifiers and binders.
  • Suitable solvents and liquid carriers are water and organic solvents, such as mineral oil fractions of medium to high boiling point, e. g. kerosene, diesel oil; oils of vegetable or animal origin; aliphatic, cyclic and aromatic hydrocarbons, e. g. toluene, paraffin,
  • tetrahydronaphthalene alkylated naphthalenes
  • alcohols e. g. ethanol, propanol, butanol, benzyl alcohol, cyclohexanol
  • glycols DMSO; ketones, e. g. cyclohexanone; esters, e. g.
  • lactates carbonates, fatty acid esters, gamma-butyrolactone; fatty acids; phosphonates;
  • amines e. g. N-methyl pyrrolidone, fatty acid dimethyl amides; and mixtures thereof.
  • Suitable solid carriers or fillers are mineral earths, e. g. silicates, silica gels, talc, kaolins, limestone, lime, chalk, clays, dolomite, diatomaceous earth, bentonite, calcium sulfate, magnesium sulfate, magnesium oxide; polysaccharides, e. g. cellulose, starch; fertilizers, e. g. ammonium sulfate, ammonium phosphate, ammonium nitrate, ureas; products of vegetable origin, e. g. cereal meal, tree bark meal, wood meal, nutshell meal, and mixtures thereof.
  • mineral earths e. g. silicates, silica gels, talc, kaolins, limestone, lime, chalk, clays, dolomite, diatomaceous earth, bentonite, calcium sulfate, magnesium sulfate, magnesium oxide
  • polysaccharides e. g. cellulose, star
  • Suitable surfactants are surface-active compounds, such as anionic, cationic, nonionic and amphoteric surfactants, block polymers, polyelectrolytes, and mixtures thereof. Such surfactants can be used as emulsifier, dispersant, solubilizer, wetter, penetration enhancer, protective colloid, or adjuvant. Examples of surfactants are listed in McCutcheon’s, Vol.1 : Emulsifiers & Detergents, McCutcheon’s Directories, Glen Rock, USA, 2008 (International Ed. or North American Ed.).
  • Suitable anionic surfactants are alkali, alkaline earth or ammonium salts of sulfonates, sulfates, phosphates, carboxylates, and mixtures thereof.
  • sulfonates are alkylaryl sulfonates, diphenyl sulfonates, alpha-olefin sulfonates, lignin sulfonates, sulfonates of fatty acids and oils, sulfonates of ethoxylated alkylphenols, sulfonates of alkoxylated arylphenols, sulfonates of condensed naphthalenes, sulfonates of dodecyl- and tridecylbenzenes, sulfonates of naphthalenes and alkyl naphthalenes, sulfosuccinates or sulfosuccinamates.
  • Examples of sulfates are sulfates of fatty acids and oils, of ethoxylated alkylphenols, of alcohols, of ethoxylated alcohols, or of fatty acid esters.
  • Examples of phosphates are phosphate esters.
  • Examples of carboxylates are alkyl carboxylates, and carboxylated alcohol or alkylphenol ethoxylates.
  • Suitable nonionic surfactants are alkoxylates, N-substituted fatty acid amides, amine oxides, esters, sugar-based surfactants, polymeric surfactants, and mixtures thereof.
  • alkoxylates are compounds such as alcohols, alkylphenols, amines, amides, arylphenols, fatty acids or fatty acid esters which have been alkoxylated with 1 to 50 equivalents.
  • Ethylene oxide and/or propylene oxide may be employed for the alkoxylation, preferably ethylene oxide.
  • N-substituted fatty acid amides are fatty acid glucamides or fatty acid
  • esters are fatty acid esters, glycerol esters or monoglycerides.
  • sugar-based surfactants are sorbitans, ethoxylated sorbitans, sucrose and glucose esters or alkylpolyglucosides.
  • polymeric surfactants are home- or copolymers of vinyl pyrrolidone, vinyl alcohols, or vinyl acetate.
  • Suitable cationic surfactants are quaternary surfactants, for example quaternary ammonium compounds with one or two hydrophobic groups, or salts of long-chain primary amines.
  • Suitable amphoteric surfactants are alkylbetains and imidazolines.
  • Suitable block polymers are block polymers of the A-B or A-B-A type comprising blocks of polyethylene oxide and polypropylene oxide, or of the A-B-C type comprising alkanol, polyethylene oxide and polypropylene oxide.
  • Suitable polyelectrolytes are polyacids or polybases. Examples of polyacids are alkali salts of polyacrylic acid or polyacid comb polymers. Examples of polybases are polyvinyl amines or polyethylene amines.
  • Suitable adjuvants are compounds, which have a negligible or even no pesticidal activity themselves, and which improve the biological performance of the compound I on the target.
  • examples are surfactants, mineral or vegetable oils, and other auxiliaries. Further examples are listed by Knowles, Adjuvants and additives, Agrow Reports DS256, T&F Informa UK, 2006, chapter 5.
  • Suitable thickeners are polysaccharides (e. g. xanthan gum, carboxymethyl cellulose), inorganic clays (organically modified or unmodified), polycarboxylates, and silicates.
  • Suitable bactericides are bronopol and isothiazolinone derivatives such as alkyliso- thiazolinones and benzisothiazolinones.
  • Suitable anti-freezing agents are ethylene glycol, propylene glycol, urea and glycerin.
  • Suitable anti-foaming agents are silicones, long chain alcohols, and salts of fatty acids.
  • Suitable colorants are pigments of low water solubility and water- soluble dyes.
  • examples are inorganic colorants (e. g. iron oxide, titan oxide, iron
  • organic colorants e. g. alizarin-, azo- and phthalocyanine colorants.
  • Suitable tackifiers or binders are polyvinyl pyrrolidones, polyvinyl acetates, polyvinyl alcohols, polyacrylates, biological or synthetic waxes, and cellulose ethers.
  • composition types and their preparation are:
  • a compound I and 5-15 wt% wetting agent e. g. alcohol alkoxylates
  • a water-soluble solvent e. g. alcohols
  • a compound I and 1-10 wt% dispersant e. g. polyvinyl pyrrolidone
  • organic solvent e. g. cyclohexanone
  • EC Emulsifiable concentrates
  • emulsifiers e. g. calcium dodecylbenzenesulfonate and castor oil ethoxylate
  • water-insoluble organic solvent e. g. aromatic hydrocarbon
  • Emulsions (EW, EO, ES)
  • emulsifiers e. g. calcium dodecylbenzenesulfonate and castor oil ethoxylate
  • 20-40 wt% water-insoluble organic solvent e. g. aromatic hydrocarbon
  • This mixture is introduced into water ad 100 wt% by means of an emulsifying machine and made into a homogeneous emulsion. Dilution with water gives an emulsion.
  • a compound I In an agitated ball mill, 20-60 wt% of a compound I are comminuted with addition of 2-10 wt% dispersants and wetting agents (e. g. sodium lignosulfonate and alcohol ethoxylate), 0.1-2 wt% thickener (e. g. xanthan gum) and water ad 100 wt% to give a fine active substance suspension. Dilution with water gives a stable suspension of the active substance. For FS type composition up to 40 wt% binder (e. g. polyvinyl alcohol) is added.
  • dispersants and wetting agents e. g. sodium lignosulfonate and alcohol ethoxylate
  • 0.1-2 wt% thickener e. g. xanthan gum
  • a compound I 50-80 wt% of a compound I are ground finely with addition of dispersants and wetting agents (e. g. sodium lignosulfonate and alcohol ethoxylate) ad 100 wt% and prepared as water- dispersible or water-soluble granules by means of technical appliances (e. g. extrusion, spray tower, fluidized bed). Dilution with water gives a stable dispersion or solution of the active substance.
  • dispersants and wetting agents e. g. sodium lignosulfonate and alcohol ethoxylate
  • dispersants e. g. sodium lignosulfonate
  • 1-3 wt% wetting agents e. g. alcohol ethoxylate
  • solid carrier e. g. silica gel
  • a compound I In an agitated ball mill, 5-25 wt% of a compound I are comminuted with addition of 3-10 wt% dispersants (e. g. sodium lignosulfonate), 1-5 wt% thickener (e. g. carboxymethyl cellulose) and water ad 100 wt% to give a fine suspension of the active substance. Dilution with water gives a stable suspension of the active substance.
  • dispersants e. g. sodium lignosulfonate
  • 1-5 wt% thickener e. g. carboxymethyl cellulose
  • wt% of a compound I are added to 5-30 wt% organic solvent blend (e. g. fatty acid dimethyl amide and cyclohexanone), 10-25 wt% surfactant blend (e. g. alcohol ethoxylate and arylphenol ethoxylate), and water ad 100 %. This mixture is stirred for 1 h to produce spontaneously a thermodynamically stable microemulsion.
  • organic solvent blend e. g. fatty acid dimethyl amide and cyclohexanone
  • surfactant blend e. g. alcohol ethoxylate and arylphenol ethoxylate
  • An oil phase comprising 5-50 wt% of a compound I, 0-40 wt% water insoluble organic solvent (e. g. aromatic hydrocarbon), 2-15 wt% acrylic monomers (e. g. methylmethacrylate, methacrylic acid and a di- or triacrylate) are dispersed into an aqueous solution of a protective colloid (e. g. polyvinyl alcohol). Radical polymerization results in the formation of poly(meth)acrylate microcapsules.
  • an oil phase comprising 5-50 wt% of a compound I according to the invention, 0-40 wt% water insoluble organic solvent (e. g. aromatic hydrocarbon), and an isocyanate monomer (e. g. diphenylmethene-4,4’-diisocyanatae) are dispersed into an aqueous solution of a protective colloid (e. g. polyvinyl alcohol).
  • a polyamine e. g.
  • hexamethylenediamine results in the formation of polyurea microcapsules.
  • the monomers amount to 1-10 wt%.
  • the wt% relate to the total CS composition.
  • Dustable powders (DP, DS)
  • 1-10 wt% of a compound I are ground finely and mixed intimately with solid carrier (e. g. finely divided kaolin) ad 100 wt%.
  • solid carrier e. g. finely divided kaolin
  • a compound I 0.5-30 wt% of a compound I is ground finely and associated with solid carrier (e. g. silicate) ad 100 wt%.
  • solid carrier e. g. silicate
  • Granulation is achieved by extrusion, spray-drying or fluidized bed.
  • organic solvent e. g. aromatic hydrocarbon
  • compositions types i) to xiii) may optionally comprise further auxiliaries, such as 0.1-1 wt% bactericides, 5-15 wt% anti-freezing agents, 0.1-1 wt% anti-foaming agents, and 0.1-1 wt% colorants.
  • auxiliaries such as 0.1-1 wt% bactericides, 5-15 wt% anti-freezing agents, 0.1-1 wt% anti-foaming agents, and 0.1-1 wt% colorants.
  • the agrochemical compositions generally comprise between 0.01 and 95%, preferably between 0.1 and 90%, more preferably between 1 and 70%, and in particular between 10 and 60%, by weight of active substance.
  • the active substances are employed in a purity of from 90% to 100%, preferably from 95% to 100% (according to NMR spectrum).
  • compositions in question give, after two-to-tenfold dilution, active substance concentrations of from 0.01 to 60% by weight, preferably from 0.1 to 40%, in the ready-to-use preparations.
  • Methods for applying compound I and compositions thereof, respectively, onto plant propagation material, especially seeds include dressing, coating, pelleting, dusting, and soaking as well as in-furrow application methods.
  • compound I or the compositions thereof, respectively are applied on to the plant propagation material by a method such that germination is not induced, e. g. by seed dressing, pelleting, coating and dusting.
  • the amounts of active substances applied are, depending on the kind of effect desired, from 0.001 to 2 kg per ha, preferably from 0.005 to 2 kg per ha, more preferably from 0.05 to 0.9 kg per ha, and in particular from 0.1 to 0.75 kg per ha.
  • amounts of active substance of from 0.1 to 1000 g, preferably from 1 to 1000 g, more preferably from 1 to 100 g and most preferably from 5 to 100 g, per 100 kilogram of plant propagation material (preferably seeds) are generally required.
  • the amount of active substance applied depends on the kind of application area and on the desired effect. Amounts customarily applied in the protection of materials are 0.001 g to 2 kg, preferably 0.005 g to 1 kg, of active substance per cubic meter of treated material.
  • oils, wetters, adjuvants, fertilizer, or micronutrients, and further pesticides may be added to the active substances or the compositions comprising them as premix or, if appropriate not until immediately prior to use (tank mix).
  • pesticides e. g. herbicides, insecticides, fungicides, growth regulators, safeners, biopesticides
  • These agents can be admixed with the compositions according to the invention in a weight ratio of 1 :100 to 100:1 , preferably 1 :10 to 10:1.
  • a pesticide is generally a chemical or biological agent (such as pestidal active ingredient, compound, composition, virus, bacterium, antimicrobial or disinfectant) that through its effect deters, incapacitates, kills or otherwise discourages pests.
  • Target pests can include insects, plant pathogens, weeds, mollusks, birds, mammals, fish, nematodes (roundworms), and microbes that destroy property, cause nuisance, spread disease or are vectors for disease.
  • pesticide includes also plant growth regulators that alter the expected growth, flowering, or reproduction rate of plants; defoliants that cause leaves or other foliage to drop from a plant, usually to facilitate harvest; desiccants that promote drying of living tissues, such as unwanted plant tops; plant activators that activate plant physiology for defense of against certain pests; safeners that reduce unwanted herbicidal action of pesticides on crop plants; and plant growth promoters that affect plant physiology e.g. to increase plant growth, biomass, yield or any other quality parameter of the harvestable goods of a crop plant.
  • composition according to the invention usually from a predosage device, a knapsack sprayer, a spray tank, a spray plane, or an irrigation system.
  • a predosage device usually from a knapsack sprayer, a spray tank, a spray plane, or an irrigation system.
  • agrochemical composition is made up with water, buffer, and/or further auxiliaries to the desired application concentration and the ready-to-use spray liquor or the agrochemical composition according to the invention is thus obtained.
  • 20 to 2000 liters, preferably 50 to 400 liters, of the ready-to-use spray liquor are applied per hectare of agricultural useful area.
  • composition according to the invention such as parts of a kit or parts of a binary or ternary mixture may be mixed by the user himself in a spray tank or any other kind of vessel used for applications (e. g. seed treater drums, seed pelleting machinery, knapsack sprayer) and further auxiliaries may be added, if appropriate.
  • a spray tank or any other kind of vessel used for applications (e. g. seed treater drums, seed pelleting machinery, knapsack sprayer) and further auxiliaries may be added, if appropriate.
  • one embodiment of the invention is a kit for preparing a usable pesticidal composition, the kit comprising a) a composition comprising component 1) as defined herein and at least one auxiliary; and b) a composition comprising component 2) as defined herein and at least one auxiliary; and optionally c) a composition comprising at least one auxiliary and optionally a further active component 3) as defined herein.
  • pesticides II e. g. pesticidally-active substances and biopesticides
  • the compounds I in conjunction with which the compounds I can be used, is intended to illustrate the possible combinations but does not limit them:
  • coumoxystrobin (A.1.3), dimoxystrobin (A.1.4), enestroburin (A.1.5), fenaminstrobin (A.1.6), fenoxystrobin/flufenoxystrobin (A.1.7), fluoxastrobin (A.1.8), kresoxim-methyl (A.1.9), mandestrobin (A.1.10), metominostrobin (A.1.11), orysastrobin (A.1.12), picoxystrobin
  • respiration inhibitors diflumetorim (A.4.1); nitrophenyl derivates: binapacryl (A.4.2), dinobuton (A.4.3), dinocap (A.4.4), fluazinam (A.4.5), meptyldinocap (A.4.6), ferimzone (A.4.7); organometal compounds: fentin salts, e. g. fentin-acetate (A.4.8), fentin chloride (A.4.9) or fentin hydroxide (A.4.10); ametoctradin (A.4.11); silthiofam (A.4.12);
  • benalaxyl (C.1.1), benalaxyl-M (C.1.2), kiralaxyl (C.1.3), metalaxyl (C.1.4), metalaxyl-M (C.1.5), ofurace (C.1.6), oxadixyl (C.1.7);
  • nucleic acid synthesis inhibitors hymexazole (C.2.1), octhilinone (C.2.2), oxolinic acid (C.2.3), bupirimate (C.2.4), 5-fluorocytosine (C.2.5), 5-fluoro-2-(p-tolylmethoxy)pyrimidin- 4-amine (C.2.6), 5-fluoro-2-(4-fluorophenylmethoxy)pyrimidin-4-amine (C.2.7), 5-fluoro- 2-(4-chlorophenylmethoxy)pyrimidin-4 amine (C.2.8);
  • tubulin inhibitors benomyl (D.1.1), carbendazim (D.1.2), fuberidazole (D1.3), thiabendazole (D.1.4), thiophanate-methyl (D.1.5), pyridachlometyl (D.1.6), A/-ethyl-2-[(3-ethynyl-8-methyl- 6-quinolyl)oxy]butanamide (D.1.8), A/-ethyl-2-[(3-ethynyl-8-methyl-6-quinolyl)oxy]-2- methylsulfanyl-acetamide (D.1.9), 2-[(3-ethynyl-8-methyl-6-quinolyl)oxy]-/ ⁇ /-(2- fluoroethyl)butanamide (D.1.10), 2-[(3-ethynyl-8-methyl-6-quinolyl)oxy]-/ ⁇ /-(2-fluoroethyl)-2- methoxy-acetamide (D.1.11)
  • diethofencarb (D.2.1), ethaboxam (D.2.2), pencycuron (D.2.3), fluopicolide (D.2.4), zoxamide (D.2.5), metrafenone (D.2.6), pyriofenone (D.2.7),
  • cyprodinil E.1.1
  • mepanipyrim E.1.2
  • pyrimethanil E.1.3
  • fluoroimid F.1.1
  • iprodione F.1.2
  • procymidone F.1.3
  • vinclozolin F.1.4
  • fludioxonil F.1.5
  • quinoxyfen F.2.1
  • edifenphos (G .1.1), iprobenfos (G.1.2), pyrazophos (G.1.3), isoprothiolane (G.1.4);
  • dicloran G.2.1
  • quintozene G.2.2
  • tecnazene G.2.3
  • tolclofos-methyl G.2.4
  • biphenyl G.2.5
  • chloroneb G.2.6
  • etridiazole G.2.7
  • zinc thiazole G.2.8
  • dimethomorph G.3.1
  • flumorph G.3.2
  • mandipropamid G.3.3
  • pyrimorph G.3.4
  • benthiavalicarb G.3.5
  • iprovalicarb G.3.6
  • valifenalate G.3.7
  • propamocarb (G.4.1);
  • oxathiapiprolin G.5.1
  • fluoxapiprolin G.5.3
  • 4-[1-[2- [3-(difluoromethyl)-5-methyl-pyrazol-1-yl]acetyl]-4-piperidyl]-/ ⁇ /-tetralin-1-yl-pyridine-2- carboxamide G.5.4
  • 4-[1-[2-[3,5-bis(difluoromethyl)pyrazol-1-yl]acetyl]-4-piperidyl]-/ ⁇ /- tetralin-1-yl-pyridine-2-carboxamide G.5.5
  • 4-[1-[2-[3-(difluoromethyl)-5-(tri- fluoromethyl)pyrazol-1-yl]acetyl]-4-piperidyl]-/ ⁇ /-tetralin-1-yl-pyridine-2-carboxamide G.5.6
  • organochlorine compounds anilazine (H.3.1), chlorothalonil (H.3.2), captafol (H.3.3), captan (H.3.4), folpet (H.3.5), dichlofluanid (H.3.6), dichlorophen (H.3.7), hexachlorobenzene (H.3.8), pentachlorphenole (H.3.9) and its salts, phthalide (H.3.10), tolylfluanid (H.3.11);
  • guanidine H.4.1
  • dodine H.4.2
  • dodine free base H.4.3
  • guazatine H.4.4
  • guazatine-acetate H.4.5
  • iminoctadine H.4.6
  • iminoctadine-triacetate H.4.7
  • iminoctadine-tris(albesilate) H.4.8
  • dithianon H.4.9
  • 2,6-dimethyl-1H,5H-[1 ,4]di- thiino[2,3-c:5,6-c']dipyrrole-1 ,3,5,7(2H,6H)-tetraone H.4.10);
  • - melanin synthesis inhibitors pyroquilon (1.2.1), tricyclazole (1.2.2), carpropamid (1.2.3), dicyclomet (1.2.4), fenoxanil (1.2.5);
  • abscisic acid M.1.1
  • amidochlor ancymidol
  • 6-benzylaminopurine brassinolide, butralin
  • chlormequat chlormequat chloride, choline chloride, cyclanilide, daminozide, dikegulac, dimethipin, 2,6-dimethylpuridine, ethephon, flumetralin, flurprimidol, fluthiacet, forchlorfenuron, gibberellic acid, inabenfide, indole-3-acetic acid , maleic hydrazide, mefluidide, mepiquat, mepiquat chloride, naphthaleneacetic acid, A/-6-benzyladenine, paclobutrazol, prohexadione, prohexadione-calcium, prohydrojasmon, thidiazuron, triapenthenol, tributyl phosphorotrithioate, 2,3,5-
  • Lipid biosynthesis inhibitors alloxydim, alloxydim-sodium, butroxydim, clethodim,
  • clodinafop clodinafop-propargyl, cycloxydim, cyhalofop, cyhalofop-butyl, diclofop, diclofop- methyl, fenoxaprop, fenoxaprop-ethyl, fenoxaprop-P, fenoxaprop-P-ethyl, fluazifop, fluazifop- butyl, fluazifop-P, fluazifop-P-butyl, haloxyfop, haloxyfop-methyl, haloxyfop-P, haloxyfop-P- methyl, metamifop, pinoxaden, profoxydim, propaquizafop, quizalofop, quizalofop-ethyl, quizalofop-tefuryl, quizalofop-P, quizalofop-P-ethyl,
  • N.2 ALS inhibitors amidosulfuron, azimsulfuron, bensulfuron, bensulfuron-methyl, chlorimuron, chlorimuron-ethyl, chlorsulfuron, cinosulfuron, cyclosulfamuron, ethametsulfuron, ethamet- sulfuron-methyl, ethoxysulfuron, flazasulfuron, flucetosulfuron, flupyrsulfuron, flupyrsulfuron- methyl-sodium, foramsulfuron, halosulfuron, halosulfuron-methyl, imazosulfuron, iodosulfu- ron, iodosulfuron-methyl-sodium, iofensulfuron, iofensulfuron-sodium, mesosulfuron, meta- zosulfuron, metsulfuron, metsulfuron-methyl, nic
  • N.3 Photosynthesis inhibitors amicarbazone; chlorotriazine; ametryn, atrazine, chloridazone, cyanazine, desmetryn, dimethametryn.hexazinone, metribuzin, prometon, prometryn, pro- pazine, simazine, simetryn, terbumeton, terbuthylazin, terbutryn, trietazin; chlorobromuron, chlorotoluron, chloroxuron, dimefuron, diuron, fluometuron, isoproturon, isouron, linuron, metamitron, methabenzthiazuron, metobenzuron, metoxuron, monolinuron, neburon, sidu- ron, tebuthiuron, thiadiazuron, desmedipham, karbutilat, phenmedipham, phenmedipham- ethyl, bromofenoxim, brom
  • N.4 protoporphyrinogen-IX oxidase inhibitors acifluorfen, acifluorfen-sodium, azafenidin, ben- carbazone, benzfendizone, bifenox, butafenacil, carfentrazone, carfentrazone-ethyl, chlor- methoxyfen, cinidon-ethyl, fluazolate, flufenpyr, flufenpyr-ethyl, flumiclorac, flumiclorac-pen- tyl, flumioxazin, fluoroglycofen, fluoroglycofen-ethyl, fluthiacet, fluthiacet-methyl, fomesafen, halosafen, lactofen, oxadiargyl, oxadiazon, oxyfluorfen, pentoxazone, profluazol, pyraclonil, pyraflufen, pyraflufen
  • N.5 Bleacher herbicides beflubutamid, diflufenican, fluridone, flurochloridone, flurtamone,
  • norflurazon picolinafen, 4-(3-trifluoromethyhphenoxy)-2-(4-trifluoromethylphenyl)pyrimidine (180608-33-7); benzobicyclon, benzofenap, bicyclopyrone, clomazone, fenquintrione, isoxaflutole, mesotrione, pyrasulfotole, pyrazolynate, pyrazoxyfen, sulcotrione, tefuryltrione, tembotrione, tolpyralate, topramezone; aclonifen, amitrole, flumeturon;
  • N.6 EPSP synthase inhibitors glyphosate, glyphosate-isopropylammonium, glyposate- potassium, glyphosate-trimesium (sulfosate);
  • Glutamine synthase inhibitors bilanaphos (bialaphos), bilanaphos-sodium, glufosinate, glufosinate-P, glufosinate-ammonium;
  • Mitosis inhibitors benfluralin, butralin, dinitramine, ethalfluralin, fluchloralin, oryzalin, pen- dimethalin, prodiamine, trifluralin; amiprophos, amiprophos-methyl, butamiphos; chlorthal, chlorthal-dimethyl, dithiopyr, thiazopyr, propyzamide, tebutam; carbetamide, chlorpropham, flamprop, flamprop-isopropyl, flamprop-methyl, flamprop-M-isopropyl, flamprop-M-methyl, propham;
  • N.10 VLCFA inhibitors acetochlor, alachlor, butachlor, dimethachlor, dimethenamid, dimethen- amid-P, metazachlor, metolachlor, metolachlor-S, pethoxamid, pretilachlor, propachlor, prop- isochlor, thenylchlor, flufenacet, mefenacet, diphenamid, naproanilide, napropamide, napro- pamide-M, fentrazamide, anilofos, cafenstrole, fenoxasulfone, ipfencarbazone, piperophos, pyroxasulfone, isoxazoline compounds of the formulae 11.1 , II.2, II.3, II.4, II.5, II.6, II.7, II.8 and II.9
  • N.11 Cellulose biosynthesis inhibitors chlorthiamid, dichlobenil, flupoxam, indaziflam, isoxaben, triaziflam, 1-cyclohexyl-5-pentafluorphenyloxy-14-[1 ,2,4,6]thiatriazin-3-ylamine (175899-01- 1);
  • N.12 Decoupler herbicides dinoseb, dinoterb, DNOC and its salts
  • N.13 Auxinic herbicides 2,4-D and its salts and esters, clacyfos, 2,4-DB and its salts and
  • esters aminocyclopyrachlor and its salts and esters, aminopyralid and its salts such as aminopyralid-dimethylammonium, aminopyralid-tris(2-hydroxypropyl)ammonium and its esters, benazolin, benazolin-ethyl, chloramben and its salts and esters, clomeprop, clopy- ralid and its salts and esters, dicamba and its salts and esters, dichlorprop and its salts and esters, dichlorprop-P and its salts and esters, fluroxypyr, fluroxypyr-butometyl, fluroxypyr- meptyl, halauxifen and its salts and esters (943832-60-8); MCPA and its salts and esters, MCPA-thioethyl, MCPB and its salts and esters, mecoprop and its salts and esters, meco- prop-P and its salts and esters, picloram and
  • Acetylcholine esterase (AChE) inhibitors aldicarb (0.1.1), alanycarb (0.1.2), bendiocarb
  • GABA-gated chloride channel antagonists endosulfan (0.2.1), chlordane (0.2.2), ethiprole (0.2.3), fipronil (0.2.4), flufiprole (0.2.5), pyrafluprole (0.2.6), pyriprole (0.2.7);
  • Nicotinic acetylcholine receptor agonists acetamiprid (0.4.1), clothianidin (0.4.2), cycloxaprid (0.4.3), dinotefuran (0.4.4), imidacloprid (0.4.5), nitenpyram (0.4.6), thiacloprid (0.4.7), thiamethoxam (0.4.8), 4,5-dihydro-/ ⁇ /-nitro-1-(2-oxiranylmethyl)-1/-/-imidazol-2-amine (0.4.9), (2£)-1-[(6-chloropyridin-3-yl)methyl]-/ ⁇ /-nitro-2-pentylidene- hydrazinecarboximidamide (0.4.10), 1-[(6-chloropyridin-3-yl)methyl]-7-methyl-8-nitro-5- propoxy-1 ,2,3,5,6,7-hexahydroimidazo[1 ,2-a]pyridine (0.4.11), nicotine (0.4.11), nicotine (0.4.11
  • Nicotinic acetylcholine receptor allosteric activators spinosad (0.5.1), spinetoram (0.5.2);
  • Chloride channel activators abamectin (0.6.1), emamectin benzoate (0.6.2), ivermectin (0.6.3), lepimectin (0.6.4), milbemectin (0.6.5);
  • 0.8 miscellaneous non-specific (multi-site) inhibitors methyl bromide (0.8.1) and other alkyl halides, chloropicrin (0.8.2), sulfuryl fluoride (0.8.3), borax (0.8.4), tartar emetic (0.8.5);
  • 0.9 Chordotonal organ TRPV channel modulators pymetrozine (0.9.1), pyrifluquinazon (0.9.2), flonicamid (0.9.3);
  • Mite growth inhibitors clofentezine (0.10.1), hexythiazox (0.10.2), diflovidazin (0.10.3), etoxazole (0.10.4);
  • Israelensis (0.11.1), Bacillus sphaericus (0.11.2), Bacillus thuringiensis subsp. aizawai (0.11.3), Bacillus thuringiensis subsp. kurstaki (0.11.4), Bacillus thuringiensis subsp.
  • Inhibitors of mitochondrial ATP synthase diafenthiuron (0.12.1), azocyclotin (0.12.2), cyhexatin (0.12.3), fenbutatin oxide (0.12.4), propargite (0.12.5), tetradifon (0.12.6);
  • Nicotinic acetylcholine receptor (nAChR) channel blockers bensultap (0.14.1), cartap hydrochloride (0.14.2), thiocyclam (0.14.3), thiosultap sodium (0.14.4);
  • Inhibitors of the chitin biosynthesis type 0 bistrifluron (0.15.1), chlorfluazuron (0.15.2), diflubenzuron (0.15.3), flucycloxuron (0.15.4), flufenoxuron (0.15.5), hexaflumuron
  • Inhibitors of the chitin biosynthesis type 1 buprofezin (0.16.1);
  • Moulting disruptors cyromazine (0.17.1); 0.18 Ecdyson receptor agonists: methoxyfenozide (0.18.1), tebufenozide (0.18.2), halofenozide (0.18.3), fufenozide (0.18.4), chromafenozide (0.18.5);
  • Octopamin receptor agonists amitraz (0.19.1);
  • Mitochondrial complex I electron transport inhibitors fenazaquin (0.21.1), fenpyroximate (0.21.2), pyrimidifen (0.21.3), pyridaben (0.21.4), tebufenpyrad (0.21.5), tolfenpyrad (0.21.6), rotenone (0.21.7);
  • Inhibitors of the of acetyl CoA carboxylase spirodiclofen (0.23.1), spiromesifen (0.23.2), spirotetramat (0.23.3), spiropidion (0.23.4);
  • Mitochondrial complex IV electron transport inhibitors aluminium phosphide (0.24.1), calcium phosphide (0.24.2), phosphine (0.24.3), zinc phosphide (0.24.4), cyanide (0.24.5);
  • Mitochondrial complex II electron transport inhibitors cyenopyrafen (0.25.1), cyflumetofen (0.25.2);
  • insecticidal active compounds of unknown or uncertain mode of action 0.28. insecticidal active compounds of unknown or uncertain mode of action: afidopyropen
  • component 2 The active substances referred to as component 2, their preparation and their activity e. g. against harmful fungi is known (cf. : http://www.alanwood.net/pesticides/); these substances are commercially available.
  • the compounds described by lUPAC nomenclature, their preparation and their pesticidal activity are also known (cf. Can. J. Plant Sci. 48(6), 587-94, 1968;
  • WO 05/123690 WO 05/63721 ; WO 05/87772; WO 05/87773; WO 06/15866; WO 06/87325; WO 06/87343; WO 07/82098; WO 07/90624, WO 10/139271 , WO 11/028657, WO 12/168188, WO 07/006670, WO 11/77514; WO 13/047749, WO 10/069882, WO 13/047441 , WO 03/16303, WO 09/90181 , WO 13/007767, WO 13/010862, WO 13/127704, WO 13/024009, WO 13/24010, WO 13/047441 , WO 13/162072, WO 13/092224, WO 11/135833, CN 1907024, CN 1456054,
  • the present invention furthermore relates to agrochemical compositions comprising a mixture of at least one compound I (component 1) and at least one further active substance useful for plant protection, e. g. selected from the groups A) to O) (component 2), in particular one further fungicide, e. g. one or more fungicide from the groups A) to K), as described above, and if desired one suitable solvent or solid carrier.
  • agrochemical compositions comprising a mixture of at least one compound I (component 1) and at least one further active substance useful for plant protection, e. g. selected from the groups A) to O) (component 2), in particular one further fungicide, e. g. one or more fungicide from the groups A) to K), as described above, and if desired one suitable solvent or solid carrier.
  • fungicide e. g. one or more fungicide from the groups A) to K
  • combating harmful fungi with a mixture of compounds I and at least one fungicide from groups A) to K), as described above, is more efficient than combating those fungi with individual compounds I or individual fungicides from groups A) to K).
  • the order of application is not essential for working of the present invention.
  • the time between both applications may vary e. g. between 2 hours to 7 days. Also, a broader range is possible ranging from 0.25 hour to 30 days, preferably from 0.5 hour to 14 days, particularly from 1 hour to 7 days or from 1.5 hours to 5 days, even more preferred from 2 hours to 1 day.
  • the weight ratio of the component 1) and the component 2) generally depends from the properties of the active components used, usually it is in the range of from 1 :10,000 to 10,000:1 , often it is in the range of from 1 :100 to 100:1 , regularly in the range of from 1 :50 to 50:1 , preferably in the range of from 1 :20 to 20:1 , more preferably in the range of from 1 :10 to 10:1 , even more preferably in the range of from 1 :4 to 4: 1 and in particular in the range of from 1 :2 to 2: 1.
  • the weight ratio of the component 1) and the component 2) usually is in the range of from 1000:1 to 1 :1 , often in the range of from 100: 1 to 1 :1 , regularly in the range of from 50:1 to 1 :1 , preferably in the range of from 20:1 to 1 :1 , more preferably in the range of from 10:1 to 1 :1 , even more preferably in the range of from 4:1 to 1 :1 and in particular in the range of from 2:1 to 1 :1.
  • the weight ratio of the component 1) and the component 2) usually is in the range of from 1 :1 to 1 :1000, often in the range of from 1 :1 to 1 :100, regularly in the range of from 1 :1 to 1 :50, preferably in the range of from 1 :1 to 1 :20, more preferably in the range of from 1 :1 to 1 :10, even more preferably in the range of from 1 :1 to 1 :4 and in particular in the range of from 1 :1 to 1 :2.
  • the ternary mixtures i.e.
  • compositions according to the invention comprising the component 1) and component 2) and a compound III (component 3), the weight ratio of component 1) and component 2) depends from the properties of the active substances used, usually it is in the range of from 1 :100 to 100:1 , regularly in the range of from 1 :50 to 50:1 , preferably in the range of from 1 :20 to 20:1 , more preferably in the range of from 1 :10 to 10:1 and in particular in the range of from 1 :4 to 4:1 , and the weight ratio of component 1) and component 3) usually it is in the range of from 1 :100 to 100:1 , regularly in the range of from 1 :50 to 50:1 , preferably in the range of from 1 :20 to 20:1 , more preferably in the range of from 1 :10 to 10:1 and in particular in the range of from 1 :4 to 4: 1.
  • any further active components are, if desired, added in a ratio of from 20:1 to 1 :20 to the component 1).
  • the present invention furthermore relates to mixtures comprising one compound of the formula I (component 1 , a group represented by the expression“(I)”) and one pesticide II (component 2), wherein pesticide II is an active ingredient selected from the groups A) to O) defined above.
  • the mixtures of active substances can be prepared as compositions comprising besides the active ingredients at least one inert ingredient (auxiliary) by usual means, e. g. by the means given for the compositions of compounds I.
  • the mixtures of active substances according to the present invention are suitable as fungicides, as are the compounds of formula I. They are distinguished by an outstanding effectiveness against a broad spectrum of phytopathogenic fungi, especially from the classes of the Ascomycetes, Basidiomycetes, Deuteromycetes and Peronosporomycetes (syn.
  • reaction mixture was quenched with 200 ml aq. NH4CI-solution and extracted with methyl-t-butylether, the organic layer was dried over sodium sulfate and concentrated. The residue was purified by column- chromatography using petrolether/methyl-t-butylether-mixtures to give 12.5 g (73% of theory) 5- cyclopropyl-2-isobutyl-2-methyl-pent-4-ynoate as yellow oil.
  • the compound was dissolved in a mixture of acetone and/or dimethylsulfoxide and the wetting agent/emulsifier Wettol, which is based on ethoxylated alkylphenoles, in a ratio (volume) solvent-emulsifier of 99 to 1 to give a total volume of 5 ml. Subsequently, water was added to total volume of 100 ml.
  • Wettol which is based on ethoxylated alkylphenoles
  • This stock solution was then diluted with the described solvent-emulsifier-water mixture to the final concentration given in the table below.
  • Example 1- Preventative fungicidal control of Botrytis cinerea on leaves of green pepper
  • Young seedlings of green pepper were grown in pots to the 4 to 5 leaf stage. These plants were sprayed to run-off with previously described spray solution, containing the concentration of active ingredient or mixture mentioned in the table below. Seven days later the plants were inoculated with an aqueous DOB solution (or a DOB solution containing 10 percent glycerine), containing the spore suspension of Botrytis cinerea. Then the plants were immediately transferred to a humid chamber. After 5 days at 22 to 24 " C and a saturated relative humidity, the extent of fungal attack on the leaves was visually assessed as % diseased leaf area.
  • aqueous DOB solution or a DOB solution containing 10 percent glycerine

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Abstract

La présente invention concerne l'utilisation de composés de formule I, dans laquelle les variables sont telles que définies dans la description et les revendications. L'invention concerne en outre les composés I et une composition pour des composés de formule I.
PCT/EP2020/064576 2019-06-06 2020-05-26 Dérivés de pyridine et leur utilisation comme fongicides Ceased WO2020244969A1 (fr)

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